885521-46-0|3-Iodo-1H-indazole-5-carboxylic acid| Ambeed

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Quality Control of [ 885521-46-0 ] Purity: 95% SDS Specification

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Product Details of [ 885521-46-0 ]

CAS No. :	885521-46-0
Formula :	C₈H₅IN₂O₂
M.W :	288.04
SMILES Code :	O=C(C1=CC2=C(NN=C2I)C=C1)O
MDL No. :	MFCD07781585
InChI Key :	DYZNTIADYAHDQK-UHFFFAOYSA-N
Pubchem ID :	24728200

Safety of [ 885521-46-0 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 885521-46-0 ] Show Less

Physicochemical Properties

Num. heavy atoms	13
Num. arom. heavy atoms	9
Fraction Csp3	0.0
Num. rotatable bonds	1
Num. H-bond acceptors	3.0
Num. H-bond donors	2.0
Molar Refractivity	55.77
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	65.98 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	0.88
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	1.77
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.87
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	1.88
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	2.33
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.75

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.19
Solubility	0.187 mg/ml ; 0.00065 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-2.77
Solubility	0.485 mg/ml ; 0.00168 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-3.23
Solubility	0.17 mg/ml ; 0.00059 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	Yes
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-6.8 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	0.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.56

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	1.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<0.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.88

Application In Synthesis of [ 885521-46-0 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 885521-46-0 ]

[ 885521-46-0 ] Synthesis Path-Downstream 1~35

1
[ 885521-46-0 ]
[ 373384-18-0 ]
[ 1338795-17-7 ]

Yield	Reaction Conditions	Operation in experiment
86%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; at 120℃; for 6h;Sealed; Microwave irradiation;	Method C (Suzuki-Miyaura cross coupling)A mixture of 3-iodo-lH-indazole (1.0 equiv), 3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)benzenesulfonamide (1.2 equiv), base and palladium catalyst (0.05 equiv) in solvents was degassed with Ar and heated sealed in a Biotage microwave reactor. The crude material after filtration through Celite using MeOH to rinse the pad. In the majority of examples, purification by preparative HPLC provided the target material.To a mixture of arylboronic acid (5 mmol) and glyoxylic acid monohydrate (460 mg, 5 mmol) in CH2CI2 (25 mL) was added dialkylamine (5 mmol). The resulting mixture was stirred overnight at rt. After evaporation of solvents, it was used as crude or purified by column chromatography.Synthesis of 3-(3-(methylsulfonyl)phenyl)-lH-indazole-5-carboxylic acidThe title compound was synthesized according to the General Method C, utilizing 3-iodo- lH-indazole-5-carboxylic acid (1.002 g, 3.47 mmol), (3-(methylsulfonyl)phenyl)boronic acid-68-4820V.1 (891.7 mg, 4.46 mmol), Pd(PPh3)4 (107.0 mg, 0.093 mmol), toluene (7 mL), EtOH (7 mL), and saturated aqueous Na2C03 (3.5 mL). The degassed solution was sealed and heated in a microwave reactor at 120 C for 6 h. After cooling to room temperature, the mixture was diluted with Et20 (300 mL) and acidified with aqueous HC1 (1M, 25 mL) and water (50 mL).Undissolved solid was collected by filtration and rinsed with water (10 mL) and 25% EtOH / Et20 (10 mL). The separated Et20 layer was discarded since it contained only traces of product. The wet solid was transferred using a mixture of acetone, THF and DMF, and evaporated in vacuo. MeOH in Et20 (50%, 10 mL) was added and the suspension was sonicated, and filtered. The solid was rinsed with MeOH in Et20 (50%, 10 mL) to provide the title compound as an pale grey solid (946.1 mg, 86 %). NMR (400 MHz, DMSO-d6) 8 ppm 13.79 (s, 1 H), 12.95 (br.s, 1H), 8.68 (s, 1 H), 8.47 (s, 1 H), 8.35 (d, J=8.0 Hz, 1 H), 8.00 (d, J=8.5 Hz, 2 H), 7.86 (t, J=8.0 Hz, 1 H), 7.71 (d, J=9.3 Hz, 1 H), 3.31 (s, 3 H); MS ESI 317.2 [M + H]+, calcd for [Ci5H12N204S + H]+ 317.0.

References: [1]Patent: WO2011/123937,2011,A1 .Location in patent: Page/Page column 66; 68-69.

2
[ 885521-46-0 ]
[ 854750-32-6 ]
[ 1430472-97-1 ]

Yield	Reaction Conditions	Operation in experiment
38%	With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 0℃; for 1h;	The mixture of 1-cyclohexylpropan-l -amine (380 mg, 2.69 mmol), 3- iodo-lH-indazole-5-carboxylic acid (774.9 mg, 2.69 mmol), DIPEA (1.33 mL, 8.07 mmols) in DMF (8 mL) was cooled down to 0C and added TBTU (864 mg, 2.69 mmol). After stirring at 0 C for 1 h, H20 was added followed by EtOAc. The organic layer was separated and washed with H20 (3x),brine, dried over Na2S04 and concentrated under reduced pressure to provide the title compound as a light yellow solid (418 mg, 38 % yield). ? NMR (400 MHz, CDCli) delta ppm 10.65 (s, 1H), 7.92 (m, 2H), 7.54 (d, J = 8.8 Hz, 1H), 5.89 (d, J = 4.1 Hz, 1H), 4.02 (m, 1H), 1.86-1.67 (m, 6H), 1.56-1.44 (m, 2H), 1.31-1.06 (m, 4H), 0.99 (t, J= 8.2 Hz, 3H); MS ESI [M + H]+412.3, calcd for [C17H22I 3O+ H]+ 412.09.

References: [1]Patent: WO2013/53051,2013,A1 .Location in patent: Page/Page column 117; 118.

3
[ 844470-82-2 ]
[ 885521-46-0 ]
[ 1430473-46-3 ]

Yield	Reaction Conditions	Operation in experiment
75%	With bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 0 - 24℃;	The title compound was synthesized according to General Method A utili?3-iodo-lH-indazole-5-carboxylic acid (358 mg, 1.23 mmol), (S)- cyclopropyl(2-fluorophenyl) methanamine hydrochloride (250 mg, 1.23 mmol), BOP-C1 (576 mg, 1.3 mmol), DIPEA (1.08 mL, 6.19 mmol) and DMF (5 mL) at 0C. The reaction was stirred and slowly warmed to rt and stirred at 24C for 3 h. The reaction was concentrated and purified by flash chromatography (Biotage isolera 60 g C 18-HS , 5-90% MeOH in 0.1% TFA.H20) to give the title compound as an off white solid (405 mg, 75%). ? NMR (400 MHz, CD3OD) delta ppm 8.08 (s, 1 H), 7.95 (dd, J=8.8, 1.6 Hz, 1 H), 7.56-7.58 (m, 2 H), 7.26-7.31 (m, 1 H), 7.17 (t, J=7.6 Hz, 1 H), 7.09 (t, J=10 Hz, 1 H), 4.76 (d, J=9.2 Hz, 1 H), 1.41-1.50 (m, 1 H), 0.66-0.72 (m, 1 H), 0.58-0.62 (m, 1 H), 0.50-0.56 (m, 2 H); MS ESI 436.2 [M + H]+, calcd for[C18Hl5FP 30+H]+ 436.
75%	With bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 0 - 24℃; for 3h;	Synthesis of (S)-N-(cvcloprovyl(2-fluorophenyl)methyl)-3-iodo-lH-indazole-5-carboxamide The title compound was synthesized according to General Method A utilizing 3- iodo-lH-indazole-5-carboxylic acid (358 mg, 1.23 mmol), (S)-cyclopropyl(2- fluorophenyl) methanamine hydrochloride (250 mg, 1.23 mmol), BOP-C1 (576 mg, 1.3 mmol), DIPEA (1.08 mL, 6.19 mmol) and DMF (5 mL) at 0C. The reaction was stirred and slowly warmed to rt and stirred at 24C for 3 h. The reaction was concentrated and purified by flash chromatography (Biotage isolera 60 g C18-HS . 5-90% MeOH in 0.1% TFA.H20) to give the title compound as an off white solid (405 mg, 75%). NMR (400 MHz, CD3OD) 8 ppm 8.08 (s, 1 H), 7.95 (dd, .7=8.8, 1.6 Hz, 1 H), 7.56-7.58 (m, 2 H), 7.26-7.31 (m, 1 H), 7.17 (t, .7=7.6 Hz, 1 H), 7.09 (t, J=10 Hz, 1 H), 4.76 (d, .7=9.2 Hz, 1 H), 1.41-1.50 (m, 1 H), 0.66-0.72 (m, 1 H), 0.58-0.62 (m, 1 H), 0.50-0.56 (m, 2 H); MS ESI 436.2 [M + H]+, calcd for [C18H,5FrN30+H]+ 436.

References: [1]Patent: WO2013/53051,2013,A1 .Location in patent: Page/Page column 141; 142.
[2]Patent: WO2014/56083,2014,A1 .Location in patent: Page/Page column 23; 36.

4
[ 885521-46-0 ]
[ 51586-24-4 ]
[ 543-27-1 ]
[ 1430473-63-4 ]

Yield	Reaction Conditions	Operation in experiment
44%		-iodo-lH-indazole-5-carboxylic acid (1.73 g, 6.00 mmol), isobutyl chloroformate (1.57 mL, 12.0 mmol), DIPEA (2.09 mL, 1.80 mmol), and DMF (20 mL) were combined and cooled to 0 C. The reaction was stirred at 0 C for 10 min at which point 2,2,2-trifluoro-l-phenylethanamine (1.27 mg, 6.00 mmol) was added. The mixture was warmed to rt and stirred for 1.5 h, The crude reaction was subsequently diluted with EtOAc and washed with aq NaHC03 and brine. The mixture was dried over MgS04 and the solvent was removed under reduced pressure to give the title compound as a beige solid (1.45 g, 44%). The product was used without further purification. MS ESI 546.1 [M + H]+, calcd for [C21H19F3I 303 + H]+ 546.0

References: [1]Patent: WO2013/53051,2013,A1 .Location in patent: Page/Page column 146.

5
[ 885521-46-0 ]
[ 1211514-70-3 ]
[ 1527515-57-6 ]

Yield	Reaction Conditions	Operation in experiment
52%	With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 0℃; for 1h;	N-(Cyclopropyl(thiazol-2-yl)methyl)-3-iodo-1H-indazole-5-carboxamide The title compound was synthesized according to General Method A utilizing <strong>[885521-46-0]3-iodo-1H-indazole-5-carboxylic acid</strong> (255 mg, 0.88 mmol), cyclopropyl(thiazol-2-yl)methanamine (150 mg, 0.97 mmol), TBTU (310 mg, 0.97 mmol), DIPEA (0.31 mL, 1.8 mmol), and DMF (8 mL). The reaction was stirred at 0 C. for 1 h. The crude reaction was subsequently diluted with H2O. A filtration and washing (H2O) of the precipitate provided the desired product as a beige solid (195 mg, 52%). The product used without further purification. 1H NMR (400 MHz, CD3OD) delta ppm 8.16 (br. s., 1H), 7.99 (m., 1H), 7.77 (br. s., 1H), 7.46-7.67 (m, 2H), 1.45-1.68 (m, 1 H), 0.46-0.90 (m, 4H); MS ESI 425.0 [M+H]+, calcd for [C15H13IN4OS+H]+ 425.0.

References: [1]Patent: US2014/5167,2014,A1 .Location in patent: Paragraph 0257; 0258.

6
[ 885521-46-0 ]
[ 1183825-71-9 ]
[ 1430474-87-5 ]

Yield	Reaction Conditions	Operation in experiment
95%	With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 25℃; for 12h;	D. N-(l-(2-chlorophenyl)-2-methylpropyl)-3-iodo-lH-indazole-5-carboxamide The title compound was synthesized according to General Method A by using l-(2-chlorophenyl)-2- methylpropan-1 -amine (0.55 g, 2.99 mmol), DMF (11 mL), 3-iodo-lH-indazole-5-carboxylic acid (863 mg, 2.99 mmol), DIPEA (2.09 mL, 11.98 mmol) and TBTU (960 mg, 2.99 mmol). The resultant reaction mass stirred at 25C for 12 h and then quenched it in 0 (440 mL). The solid collected by filtration and was washed with H20 to provide the title compound (cream color solid, 1.29 g, 95%). NMR (400 MHz, DMSO-d6) delta 13.76 (s, 1H), 8.91 (d, .7=8.8 Hz, 1H), 7.91 (d, J=9.2 Hz, 1H), 7.74- 7.66 (m, 1H), 7.59 (d, J=8.8 Hz, 1H), 7.46-7.22 (m, 4H), 5.27 (t, J=9.2 Hz, 1H),2.20-2.15 (m, 1H), 1.08 (d, .7=6.0 Hz, 3H), 0.79 (d, J=6.8 Hz, 3H) ; MS ESI 454 [M + H]+, calcd for [Cl8H17CHN30 + H]+ 454.

References: [1]Patent: WO2014/56083,2014,A1 .Location in patent: Page/Page column 35.

7
[ 885521-46-0 ]
N-((R)-cyclopropyl(pyridin-2-yl)methyl)-3-(4-((1R,3R,5S)-3-hydroxy-8-azabicyclo[3.2.1]octan-8-yl)phenyl)-1H-indazole-5-carboxamide [ No CAS ]

References: [1]Patent: WO2014/56083,2014,A1 .

8
[ 885521-46-0 ]
N-((R)-cyclopropyl(pyridin-2-yl)methyl)-3-(4-((1R,3R,5S)-3-hydroxy-8-azabicyclo[3.2.1]octan-8-yl)phenyl)-1H-indazole-5-carboxamide dihydrochloride [ No CAS ]

References: [1]Patent: WO2014/56083,2014,A1 .

9
[ 885521-46-0 ]
[ 1430741-34-6 ]

References: [1]Patent: WO2014/56083,2014,A1 .

10
[ 885521-46-0 ]
N-((S)-cyclopropyl(pyridin-2-yl)methyl)-3-(4-((1R,3R,5S)-3-hydroxy-8-azabicyclo[3.2.1]octan-8-yl)phenyl)-1H-indazole-5-carboxamide dihydrochloride [ No CAS ]

References: [1]Patent: WO2014/56083,2014,A1 .

11
[ 885521-46-0 ]
3-(4-((1R,5S)-3-oxa-8-azabicyclo[3.2.1]octan-8-yl)phenyl)-N-((S)-cyclopropyl(2-fluorophenyl)methyl)-1H-indazole-5-carboxamide hydrochloride [ No CAS ]

References: [1]Patent: WO2014/56083,2014,A1 .

12
[ 885521-46-0 ]
[ 1213205-62-9 ]
[ 1430473-34-9 ]

Yield	Reaction Conditions	Operation in experiment
80%	With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide;	General Method A iamide coupling) A DMF solution of 3-iodo-lH-indazole-5-carboxylic acid (1.0 equiv), DIPEA (3.0-5.0 equiv) and R 'NH (1.00-1.05 equiv) at 0 C or rt was treated with TBTU or BOP-C1 (1.05 equiv) added in one portion. The reaction was stirred allowing slowly to warm to rt. After several h or overnight stirring the crude reaction was subsequently diluted with H20. In the majority of examples a filtration and washing (H20) of the precipitate provided the desired material with the required purity or alternatively the material was purified directly by prep-HPLC or/and flash chromatography.

References: [1]Patent: WO2014/56083,2014,A1 .Location in patent: Page/Page column 23; 35.

13
[ 885521-46-0 ]
[ 1430472-82-4 ]
[ 1430473-48-5 ]

Yield	Reaction Conditions	Operation in experiment
87%	With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; for 4h;	Synthesis of. fS)-N-(l-f2-fl orophenyl)-3-methylbiityl)-3-iodo-lH-ind zole-5-c rboxamide The title compound was synthesized according to General Method A by utilizing (S)-l-(2-fluorophenyl)-3-methylbutan-l-amine HCl salt (1.0 g, 0.46 mmol), 3- iodo-lH-indazole-5-carboxylic acid (1.32 g, 0.46 mmol), TBTU (1.55 g, 0.48 mmol), DIPEA (3.01 mL, 1.84 mmol) and DMF (15 mL). After stirring for 4h, the crude reaction was subsequently diluted with H20, filtered and washed with H20 to give the title compound as a cream solid (1.8 g, 87%). NMR (400 MHz, CD3OD) 5 ppm 8.95 (d, J = 8.4 Hz, 1H), 8.08 (s, 1 H), 7.93 (d, J = 8.8 Hz, 1H), (m, 1 H), 7.60-7.50 (m, 1 H), 7.47-7.56 (m, 1 H), 7.23-7.31 (m, 1 H), 7.13- 7.21 (m, 2 H), 5.41-5.53 (m, 1 H), 1.84-1.92 (m, 1 H), 1.60-1.72 (m, 1 H), 1.47-1.58 (m, 1 H), 0.89- 0.99 (m, 6 H); MS ESI 452.2 [M + H] calcd for [C,9H19FrN30+H]+ 452.06

References: [1]Patent: WO2014/56083,2014,A1 .Location in patent: Page/Page column 23; 36.

14
(S)-N-cyclopropyl-N-phenylmethylamine hydrochloride [ No CAS ]
[ 885521-46-0 ]
[ 1430473-02-1 ]

Yield	Reaction Conditions	Operation in experiment
98%	With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 0℃;	Synthesis of (S)-N-(cyclopmpyl(phenyl)methyl)-3-iodo-lH-indazole-5-carboxamide The title compound was synthesized according to the General Method A utilizing 3-iodo-lH-indazole-5-carboxylic acid (79 mg, 0.79 mmol), (s)- cycloproylphenylmethylamine FontWeight="Bold" FontSize="10" HC1 (50 mg, 0.27 mmol), TBTU (87 mg, 0.27 mmol), DIPEA (0.14 mL, 0.81 mmol), and DMF (4 mL) to give the title compound (orange solid, 110 mg, 98 %). NMR (400 MHz, CD3OD) delta ppm 8.09 (s, 1 H), 7.95 (dd, J=8.9, 1.6 Hz, 1 H), 7.56 (d, J=8.8 Hz, 1 H), 7.43 - 7.50 (m, 2 H), 7.33 (t, .7=7.6 Hz, 2 H), 7.24 (t, J=7.3 Hz, 1 H), 4.46 (d, .7=9.5 Hz, 1 H), 1.34 - 1.46 (m, 1 H), 0.66 (d, .7=8.0 Hz, 2 H), 0.48 (m, 2 H); MS ESI 418.1 [M + H] calcd for [C,8Hi6IN30 + H]+ 418.0.

References: [1]Patent: WO2014/56083,2014,A1 .Location in patent: Page/Page column 22; 34.

15
[ 885521-46-0 ]
cyclopentyl(pyrimidin-2-yl)methanamine [ No CAS ]
[ 1430474-89-7 ]