Acetic Anhydride → HCID 72704397, compound

HRID 60077Notes

Reaction equation

HRID 60077 reaction equation
[C:1]([N:5]1[CH2:11][CH:10]([N:12]2[C:16]3[C:17]([Cl:21])=[CH:18][CH:19]=[CH:20][C:15]=3[N:14]=[C:13]2[NH:22][C:23](=[O:31])[C:24]2[CH:29]=[CH:28][N:27]=[C:26]([CH3:30])[CH:25]=2)[CH2:9][NH:8][CH2:7][CH2:6]1)(=[O:4])[CH:2]=[CH2:3].C(N(CC)C(C)C)(C)C.[C:41](OC(=O)C)(=[O:43])[CH3:42]>C(Cl)Cl>[C:41]([N:8]1[CH2:9][CH:10]([N:12]2[C:16]3[C:17]([Cl:21])=[CH:18][CH:19]=[CH:20][C:15]=3[N:14]=[C:13]2[NH:22][C:23](=[O:31])[C:24]2[CH:29]=[CH:28][N:27]=[C:26]([CH3:30])[CH:25]=2)[CH2:11][N:5]([C:1](=[O:4])[CH:2]=[CH2:3])[CH2:6][CH2:7]1)(=[O:43])[CH3:42]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 72704396N-(1-(1-acryloyl-1,4-diazepan-6-yl)-7-chloro-1H-benzo[d]imidazol-2-yl)-2-methylisonicotinamide

Product 1

HCID 72704397HCID 72704397, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of Example 13 (30 mg, 0.068 mmol), N,N-dimethylaminopyridine (17 mg, 0.137 mmol), and N,N-diisopropylethylamine (0.024 mL, 0.137 mmol) in CH2Cl2 (0.75 mL) was treated at room temperature with acetic anhydride (0.01 mL, 0.103 mmol) and stirred for 5 min. The reaction was then added directly to a RediSep dry loader cartridge and purified by column chromatography (9:1:0.175 M CH2Cl2/MeOH/NH3 in CH2Cl2, 0-50%) to afford the title compound (Example 14). 1H NMR (400 MHz, MeOD) δ 8.53-8.41 (m, 1H), 7.96-7.88 (m, 1H), 7.88-7.77 (m, 1H), 7.50-7.36 (m, 1H), 7.31-7.13 (m, 2H), 6.91-6.60 (m, 1H), 6.30-6.08 (m, 1H), 5.87-5.72 (m, 1H), 5.72-5.65 (m, 1H), 4.43-4.24 (m, 4H), 4.24-3.94 (m, 2H), 3.64-3.48 (m, 2H), 2.55 (s, 3H), 2.12-1.99 (m, 3H); MS calculated for C24H26ClN6O3 (M+H+) 481.17. found 481.2.

Workup

  1. additionThe reaction was then added directly to a RediSep
  2. customdry loader cartridge
  3. custompurified by column chromatography (9:1:0.175 M CH2Cl2/MeOH/NH3 in CH2Cl2, 0-50%)

Sources & evidence

ORD record
ord-2d80dfe246d14f86831610c97b7c8194
Source dataset
uspto-grants-2016_09
Patent number
US09440957B2

Reaction notes

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