Ethanol → HCID 70979181, compound

HRID 1485446Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]3[N:17]4[C:18]([CH3:21])=[N:19][N:20]=[C:16]4[CH:15]([CH3:22])[CH2:14][N:13]([C:23]4[CH:30]=[CH:29][C:26]([C:27]#[N:28])=[CH:25][CH:24]=4)[C:12]=3[CH:31]=2)=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C([OH:53])C.O>C(OCC)(=O)C.C(O[Pd]OC(=O)C)(=O)C>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]3[N:17]4[C:18]([CH3:21])=[N:19][N:20]=[C:16]4[CH:15]([CH3:22])[CH2:14][N:13]([C:23]4[CH:24]=[CH:25][C:26]([C:27]([NH2:28])=[O:53])=[CH:29][CH:30]=4)[C:12]=3[CH:31]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 4-(8-(6-aminopyridin-3-yl)-1,4-dimethyl-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepin-6(5H)-yl)benzonitrile (150 mg, 0.37 mmol), triphenylphosphine (194 mg, 0.74 mmol) and diacetoxypalladium (8.3 mg, 0.037 mmol) in mixed solution of ethanol (6 mL) and water (2 mL) was heated at 60° C. for 30 minutes under nitrogen atmosphere. The reaction mixture was diluted with ethyl acetate (20 mL) and washed with brine (10 mL*3). The organic phase was separated, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated to give a crude product, which was purified by column chromatography (silica gel, dichloromethane/methanol=15:1) to afford 4-(8-(6-aminopyridin-3-yl)-1,4-dimethyl-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepin-6(5H)-yl)benzamide as a white solid (80 mg, 50.8%).

Workup

washwashed with brine (10 mL*3)
customThe organic phase was separated
dry with materialdried over anhydrous sodium sulfate
filtrationfiltered
concentrationThe filtrate was concentrated
customto give a crude product, which
customwas purified by column chromatography (silica gel, dichloromethane/methanol=15:1)

Sources & evidence

ORD record: ord-1a0df89ec394402a982e32445d920266
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09422292B2

Reaction notes

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