141774-70-1|(S)-tert-Butyl (pyrrolidin-2-ylmethyl)carbamate| Ambeed

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Quality Control of [ 141774-70-1 ] Purity: 95% SDS Specification

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Product Details of [ 141774-70-1 ]

CAS No. :	141774-70-1
Formula :	C₁₀H₂₀N₂O₂
M.W :	200.28
SMILES Code :	O=C(OC(C)(C)C)NC[C@H]1NCCC1
MDL No. :	MFCD06796572
InChI Key :	DPJPFGHHTJLWQQ-QMMMGPOBSA-N
Pubchem ID :	22869529

Safety of [ 141774-70-1 ]

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

Application In Synthesis of [ 141774-70-1 ]

* 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 [ 141774-70-1 ]

[ 141774-70-1 ] Synthesis Path-Downstream 1~35

1
[ 141774-70-1 ]
[ 288083-40-9 ]
[ 1186121-15-2 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 4034 - 4041.

2
[ 141774-70-1 ]
[ 1314605-39-4 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 3627 - 3631.

3
[ 141774-70-1 ]
C₂₆H₃₂N₄O [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 3627 - 3631.

4
[ 141774-70-1 ]
[ 1301177-27-4 ]
C₃₁H₄₁BrN₄O₃ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 3627 - 3631.

5
[ 141774-70-1 ]
[ 1611493-97-0 ]
[ 1611494-01-9 ]

References: [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 4772 - 4795.

6
[ 853029-57-9 ]
[ 141774-70-1 ]
C₃₀H₃₆N₈O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide; at 75.0℃; for 6h;	A mixture of 4b (88 mg, 0.2 mmol), (S)-3-(N-Boc-amino)piperidine (44 mg, 0.22 mmol) and K2CO3 (55 mg, 0.4 mmol) in DMF (6 mL) was stirred at 75 C for 6 h. After cooling to r.t., the mixture was poured into water (12 mL) and extracted with DCM (3 * 10 mL). The combined organic layer was washed with saturated brine, dried over anhydrous Na2SO4, and concentrated. The crude product was purified by flash chromatography (petroleum ether/ethyl acetate, 1:1) to give the Boc precursor of 1i as a colorless syrup (80 mg, 72%), which was dissolved in DCM (2 mL), and TFA (390 muL) was added. The solution was stirred at room temperature for 3 h and then poured into ice-cold water (4 mL). The organic phase was separated, and the aqueous phase was basified with K2CO3 and extracted with DCM (2 * 10 mL). The organic layers were combined and washed with saturated brine, dried over anhydrous Na2SO4, and concentrated. The crude product was purified by flash chromatography (DCM/MeOH/TEA, 100:0.5:0.5) to give pure 1i as a white solid (51 mg, 85%).

References: [1]European Journal of Medicinal Chemistry,2014,vol. 83,p. 547 - 560.

7
[ 141774-70-1 ]
[ 1262215-68-8 ]
4-[(S)-2-(tert-butoxycarbonylamino-methyl)-pyrrolidin-1-ylmethyl]-3-trifluoromethyl-benzoic acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With sodium tris(acetoxy)borohydride; In tetrahydrofuran; at 20.0℃; for 1h;	[Example 119] Compound b32 4-[(S)-2-(tert-Butoxycarbonylamino-methyl)-pyrrolidin-1-ylmethyl]-3-trifluoromethyl-benzoic acid ethyl ester [0400] (S)-1-Pyrrolidin-2-ylmethyl-carbamic acid tert-butyl ester (488 mg, 2.4 mmol) and sodium triacetoxyborohydride (516 mg, 2.4 mmol) were added to a solution of 4-formyl-3-trifluoromethyl-benzoic acid ethyl ester (Compound b31, 200 mg, 0.81 mmol) in THF (8 ml), and the mixture was stirred at room temperature for one hour. The reaction solution was diluted with ethyl acetate, and the organic layer was washed with a saturated aqueous sodium bicarbonate solution, water, and saturated saline, and then dried over anhydrous sodium sulfate. The drying agent was removed by filtration. After concentration under reduced pressure, the resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane) to yield the title compound (265 mg, 76%) as an oily substance. 1H-NMR (300 MHz, CDCl3) delta: 8.29 (1H, s), 8.18 (1H, d, J = 8.2 Hz), 7.85 (1H, d, J = 8.2 Hz), 4.83 (1H, brs), 4.41 (2H, q, J = 7.2 Hz), 4.11 (1H, d, J = 14.8 Hz), 3.63 (1H, d, J = 14.8 Hz), 3.37-3.26 (1H, m), 3.14-3.06 (1H, m), 2.95-2.89 (1H, m), 2.82-2.72 (1H, m), 2.23-2.14 (1H, m), 1.99-1.89 (1H, m), 1.78-1.62 (3H, m), 1.44 (9H, s), 1.41 (3H, t, J = 7.2 Hz)

References: [1]Patent: EP2842939,2015,A1 .Location in patent: Paragraph 0400; 0401.

8
[ 141774-70-1 ]
[ 67-64-1 ]
tert-butyl (S)-((1-isopropylpyrrolidin-2-yl)methyl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%		<strong>[141774-70-1](S)-2-N-Boc-aminomethylpyrrolidine</strong> (5.00 g, 25.0 mmol, 1.00 eq), acetone (3.10 mL, 49.9 mmol, 2.00 eq) and acetic acid (3.57 ml, 62.4 mmol, 2.50 eq) were dissolved in DCM (125 mL) and stirred at room temperature for three hours. Sodium triacetoxyborohydride (7.94 g, 37.4 mmol, 1.50 eq) was added and the reaction was allowed to stir overnight. The reaction was washed with saturated sodium bicarbonate and the layers separated. The aqueous layer was extracted with 3 : 1 CHCI3/IPA (3 : 1) (2x) and the combined organics were dried (MgS04), filtered and concentrated in vacuo. Purification by flash chromatography on silica gel using 0-90% DCM/MeOH/NH4OH (89: 10: 1) afforded 6.09 g (100%) of the title compound as a white solid: 1H MR (400 MHz, DMSO-d6) delta 6.69 (t, J= 5.4 Hz, 1H), 2.97-2.91 (m, 1H), 2.77 (t, J= 6.0 Hz, 2H), 2.74-2.67 (m, 1H), 2.61-2.54 (m, 1H), 2.42-2.33 (m, 1H), 1.63-1.50 (m, 4H), 1.36 (s, 9H), 1.03 (d, J= 6.4 Hz, 3H), 0.92 (d, J= 6.4 Hz, 3H); ES-MS [M+l]+: 243.4.

References: [1]Patent: WO2017/117556,2017,A1 .Location in patent: Paragraph 00248.

9
[ 141774-70-1 ]
(S)-2-cyclopentyl-N-((1-isopropylpyrrolidin-2-yl)methyl)-10-methyl-1-oxo-1,2-dihydropyrazino[1,2-a]indole-4-carboxamide [ No CAS ]

References: [1]Patent: WO2017/117556,2017,A1 .

10
[ 141774-70-1 ]
(S)-(1-isopropylpyrrolidin-2-yl)methanamine dihydrochloride [ No CAS ]

References: [1]Patent: WO2017/117556,2017,A1 .

11
[ 141774-70-1 ]
[ 4023-02-3 ]
tert-butyl N-[[(2S)-1-carbamimidoylpyrrolidin-2-yl]methyl]carbamate hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20.0℃; for 96h;	A 100 mL round-bottom flask flask was charged with a solution of tert-butyl N- [[(2S)-pyrrolidin-2-yl]methyl]carbamate (1 g, 4.993 mmol) in DMF (3 mL), then was added pyrazole-1-carboxamidine hydrochloride (0.7319 g, 4.993 mmol) and N,N- diisopropylethylamine (0.6453 g, 4.993 mmol). The reaction was stirred at ambient temperature for 4 days, then diluted with 50 mL of diethyl ether. The mixture was stirred for 2 h, then the solvents were decanted to leave an oil. This was taken up in 2 mL of ethanol, then the solution was diluted with 25 mL of ethyl acetate and 10 mL of hexanes. The solvents were decanted, and the residue was dried in vacuo to give tert-butyl N-[[(2S)-1-carbamimidoylpyrrolidin-2- yl]methyl]carbamate hydrochloride (1.058 g, 76 % yield) as an off-white foam.

References: [1]Patent: WO2018/39539,2018,A1 .Location in patent: Paragraph 00203.

12
[ 7531-52-4 ]
[ 141774-70-1 ]

References: [1]Patent: US2018/72743,2018,A1 .

13
[ 141774-70-1 ]
1-((R)-1-(2,4-dichlorophenyl)ethyl)-6-(5-methyl-4-oxocyclohex-1-en-1-yl)-1H-pyrazolo[3,4-b]pyrazine-3-carbonitrile [ No CAS ]
6-((4S,5R)-4-((S)-2-(aminomethyl)pyrrolidin-1-yl)-5-methylcyclohex-1-en-1-yl)-1-((R)-1-(2,4-dichlorophenyl)ethyl)-1H-pyrazolo[3,4-b]pyrazine-3-carbonitrile hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		The title compound was synthesized by combining <strong>[141774-70-1]tert-butyl (S)-(pyrrolidin-2-ylmethyl)carbamate</strong> (Example 81, Step 4, 62 mg, 0.31 mmol) with 1-((R)-1-(2,4-dichlorophenyl)ethyl)-6-(5-methyl-4-oxocyclohex-1-en-1-yl)-1H-pyrazolo[3,4-b]pyrazine-3-carbonitrile (Example 75, Step 1, 120 mg, 0.28 mmol) in 1,2-dichloroethane (1.1 mL). The reaction turned a dark red color. Then, NaBH(OAc)3 (120 mg, 0.56 mmol) was added, and the reaction turned a deep purple color. The reaction was then stirred overnight at room temperature. The reaction was diluted with saturated aqueous sodium bicarbonate and was extracted with dichloromethane (3), washing with brine and dried over anhydrous sodium sulfate. The organic solvent was removed under reduced pressure, and the crude residue was purified by reverse phase preparative HPLC (Phenomenex Gemini-NX, 10a, C18, 110A, 25030 mm, eluent: 0% to 100% acetonitrile in water, both eluents containing 0.1% trifluoroacetic acid, gradient elution over 30 min), which separated the diastereomers and afforded the title compound as the second eluting peak out of three UV peaks. The residue was then subjected to 4 N HCl in 1,4-dixoane and stirred for 3 h before being concentrated under reduced pressure. This oil was rinsed with acetonitrile to remove an impurity, leaving the title compound as the final product. 1H NMR (400 MHz; CD3OD; HCl salt) delta 9.10 (s, 1H), 7.50 (d, J=2.1 Hz, 1H), 7.45 (d, J=8.5 Hz, 1H), 7.34 (dd, J=8.5, 2.1 Hz, 1H), 6.99-6.93 (m, 1H), 6.74 (q, J=7.0 Hz, 1H), 4.27-4.18 (m, 1H), 3.86-3.77 (m, 2H), 3.77-3.70 (m, 2H), 3.69-3.63 (m, 4H), 3.60-3.54 (m, 2H), 3.49-3.38 (m, 2H), 2.96-2.82 (m, 2H), 2.74-2.62 (m, 1H), 2.44-2.30 (m, 1H), 2.28-2.08 (m, 2H), 2.01 (d, J=7.1 Hz, 3H), 1.18 (d, J=6.0 Hz, 3H); m/z 510.1 (M+H+).

References: [1]Journal of Medicinal Chemistry,2019,vol. 62,p. 6190 - 6213.
[2]Patent: US2018/72743,2018,A1 .Location in patent: Paragraph 1727-1728.

14
[ 141774-70-1 ]
1-((R)-1-(2,4-dichlorophenyl)ethyl)-6-(5-methyl-4-oxocyclohex-1-en-1-yl)-1H-pyrazolo[3,4-b]pyrazine-3-carbonitrile [ No CAS ]
N-(((S)-1-((1S,6R)-4-(3-cyano-1-((R)-1-(2,4-dichlorophenyl)ethyl)-1H-pyrazolo[3,4-b]pyrazin-6-yl)-6-methylcyclohex-3-en-1-yl)pyrrolidin-2-yl)methyl)methanesulfonamide hydrochloride [ No CAS ]

References: [1]Patent: US2018/72743,2018,A1 .

15
[ 114883-85-1 ]
[ 141774-70-1 ]

References: [1]Patent: US2018/72743,2018,A1 .

16
[ 96948-23-1 ]
[ 141774-70-1 ]

References: [1]Patent: US2018/72743,2018,A1 .

17
[ 342876-81-7 ]
[ 141774-70-1 ]

Yield	Reaction Conditions	Operation in experiment
	With 10 wt% Pd(OH)2 on carbon; hydrogen; acetic acid; In ethanol;	The product of Example 81, Step 3, tert-butyl (S)-((1-benzylpyrrolidin-2-yl)methyl)carbamate (5.0 g, 17 mmol) and 20% palladium hydroxide on carbon (500 mg, 0.70 mmol) were diluted with a solution of ethanol (35 mL) and acetic acid (15 mL). Hydrogen gas was then bubbled through the solution for 2 h before the reaction mixture was stirred under a hydrogen atmosphere overnight. The reaction was filtered through Celite, and the product was used directly in the next step.

References: [1]Patent: US2018/72743,2018,A1 .Location in patent: Paragraph 1725-1726.

18
[ 141774-70-1 ]
(S)-(1-(6-chloro-1-(4-fluoro-3,5-dimethylbenzyl)-2-(piperazin-1-yl)-1H-benzo[d]imidazol-4-yl)pyrrolidin-2-yl)methanamine [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 8875 - 8894.

19
[ 141774-70-1 ]
(S)-(1-(6-chloro-1-(4-fluoro-3,5-dimethylbenzyl)-2-(piperazin-1-yl)-1H-benzo[d]imidazol-4-yl)pyrrolidin-2-yl)methanamine trifluoroacetate [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 8875 - 8894.

20
[ 141774-70-1 ]
tert-butyl-4-(4-bromo-6-chloro-1-(4-fluoro-3,5-dimethylbenzyl)-1H-benzo[d]imidazol-2-yl)piperazine-1-carboxylate [ No CAS ]
C₃₅H₄₈ClFN₆O₄ [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 8875 - 8894.

21
[ 141774-70-1 ]
(S)-tert-butyl (1-(2-amino-3-(methylamino)-6-nitrophenyl)pyrrolidin-2-yl)methylcarbamate [ No CAS ]