Acetic Acid → HCID 86694414, compound

HRID 535424Notes

Reaction equation

[NH2:1][CH:2]([CH3:27])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[C:13]([CH3:18])=[N:14][O:15][C:16]=2[CH3:17])=[C:8]([C:19]#[C:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:7]=1)=[O:4].[CH3:28][C:29](=O)[CH3:30].C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[CH3:18][C:13]1[C:12]([C:9]2[CH:10]=[CH:11][C:6]([NH:5][C:3](=[O:4])[CH:2]([NH:1][CH:29]([CH3:30])[CH3:28])[CH3:27])=[N:7][C:8]=2[C:19]#[C:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[C:16]([CH3:17])[O:15][N:14]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 2-amino-N-[5-(3,5-dimethyl-1,2-oxazol-4-yl)-6-(2-phenylethynyl)pyridin-2-yl]propanamide (example 165, 20 mg, 0.06 mmol), propan-2-one (16.2 ml, 0.28 mmol), acetic acid (4 μl, 0.07 mmol), MeOH (0.5 ml) and sodium cyanoborohydride (5.5 mg, 0.08 mmol) is stirred at 50° C. for 30 minutes. The reaction mixture is concentrated in vacuo and the product purified by RP HPLC. Yield: 11 mg (48%). HPLC-MS: M+H=403; tR=1.52 min (*Method—1).

Workup

concentrationThe reaction mixture is concentrated in vacuo
customthe product purified by RP HPLC

Sources & evidence

ORD record: ord-acfbf46ae38947e9b50bad89abc7750d
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08859541B2

Reaction notes

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