CAS No. :	639091-78-4
Formula :	C₁₁H₁₇N₃O₂
M.W :	223.27
SMILES Code :	C(C)(C)(C)OC(NC1=NC=CC(=C1)CN)=O
MDL No. :	MFCD06213871
InChI Key :	MTLPTFRZCYSDNT-UHFFFAOYSA-N
Pubchem ID :	21068468

Safety of [ 639091-78-4 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H332-H335
Precautionary Statements:	P280-P305+P351+P338-P310

Application In Synthesis of [ 639091-78-4 ]

* 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.

Upstream synthesis route of [ 639091-78-4 ]
Downstream synthetic route of [ 639091-78-4 ]

[ 639091-78-4 ] Synthesis Path-Upstream 1~7

1
[ 856897-86-4 ]
[ 639091-78-4 ]

Yield	Reaction Conditions	Operation in experiment
85%	With sodium tetrahydroborate; water In tetrahydrofuran at 20℃; for 4 h;	(b) (4-Aminomethylperidin-2-Yl . carbamic acid tert-butyl ester; A solution of sodium borohydride (0.92 g, 24 mmol) in water (25 mL) was added to a slurry of Pd/C (10percent, 50 mg) in water (25 mL) under stirring. Next, (4-azidomethylpyridin-2-yl) carbamic acid tert-butyl ester (0.40 g, 6.1 mmol; see step (a) above) in THF (75 mL) was added dropwise rather rapidly under ice-cooling. The reaction was stirred at room temperature for 4 hours. An aqueous solution of sodium hydrogensulfate was added slowly to give an acidic pH. The reaction mixture was suction filtered through a CelitetE) pad which was further washed with water. The combined aqueous layer was washed with ethyl acetate, made alkaline by addition of NaOH (aq. ) and extracted with ethyl acetate (3x). The combined organic phases were washed with water, dried (Na2S04), filtered and the solvent was evaporated under reduced pressure. The crude product (1. 1 g, 85percent) crystallised and was used without further purification. IH NMR (300 MHz, CDC13) 5 10.06 (m, 1H), 8. 25 (m, 1H), 7.94 (m, 1H), 6. 88 (m, 1H), 3.83 (bs, 2H), 1.50 (s, 9H).
85%	Stage #1: With sodium tetrahydroborate In tetrahydrofuran; water at 0 - 20℃; for 4 h; Stage #2: With sodium hydrogen sulfate In tetrahydrofuran; waterAcidic aqueous solution Stage #3: With sodium hydroxide In waterAlkaline aqueous solution	b) (4-Aminomethylpyridin-2-yl) carbamic acid tert-butyl ester; A solution of sodium borohydride (0.92 g, 24 mmol) in water (25 mL) was added to a slurry of Pd/C (10percent, 50 mg) in water (25 mL) under stirring. Next, (4-azidomethylpyridin-2-yl) carbamic acid ter-butyl ester (0.40 g, 6.1 mmol; see step (a) above) in THF (75 mL) was added dropwise rather rapidly under ice-cooling. The reaction was stirred at room temperature for 4 hours. An aqueous solution of sodium hydrogensulfate was added slowly to give an acidic pH. The reaction mixture was suction filtered through a Celite pad which was further washed with water. The combined aqueous layer was washed with ethyl acetate, made alkaline by addition of NaOH (aq. ) and extracted with ethyl acetate (3x). The combined organic phases were washed with water, dried (Na2SO4), filtered and the solvent was evaporated under reduced pressure. The crude product (1.1 g, 85percent) crystallised and was used without further purification. 1H NMR (300 MHz, CDC13) 5 10.06 (m, 1H), 8. 25 (m, 1H), 7.94 (m, 1H), 6. 88 (m, 1H), 3.83 (bs, 2H), 1.50 (s, 9H).

References: [1] Patent: WO2005/75424, 2005, A1, . Location in patent: Page/Page column 108.
[2] Patent: WO2005/58826, 2005, A1, . Location in patent: Page/Page column 99-100.

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[ 639091-77-3 ]
[ 639091-78-4 ]