Acetyl chloride → HCID 59618662, compound

HRID 1691456Notes

Reaction equation

HRID 1691456 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([N:14]2[C:20]3[CH:21]=[C:22]([C:25]([NH:27][NH2:28])=[O:26])[CH:23]=[CH:24][C:19]=3[NH:18][C:17]3[N:29]=[C:30]([C:33]([F:36])([F:35])[F:34])[CH:31]=[CH:32][C:16]=3[CH2:15]2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:37](N(CC)CC)[CH3:38].C(Cl)(=O)C.O=P(Cl)(Cl)Cl>C1COCC1.C(#N)C>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([S:11]([N:14]2[C:20]3[CH:21]=[C:22]([C:25]4[O:26][C:37]([CH3:38])=[N:28][N:27]=4)[CH:23]=[CH:24][C:19]=3[NH:18][C:17]3[N:29]=[C:30]([C:33]([F:35])([F:36])[F:34])[CH:31]=[CH:32][C:16]=3[CH2:15]2)(=[O:13])=[O:12])=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 669016526-[(4-tert-butylphenyl)sulfonyl]-2-(trifluoromethyl)-6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepine-8-carbohydrazide2×

Product 1

HCID 59618662HCID 59618662, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-[(4-tert-butylphenyl)sulfonyl]-2-(trifluoromethyl)-6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepine-8-carbohydrazide (intermediate 57, 0.040 g, 0.0771 mmol) and triethylamine (0.038 mL) in THF (0.65 mL) at rt was added acetyl chloride (8.5 mg, 0.108 mmol), and the reaction was stirred at rt overnight. The volatiles were removed and the residue was chromatographed on a SiO2 column to provide acetyl product, which was mixed with POCl3 (60 mg, 0.4 mmol) and acetonitrile (0.14 mL), and was stirred at 80° C. for 3 h. The volatiles were removed, and the residue was purified by SiO2 column chromatography to provide the title compound. LC/MS: m/e 544.1 (M+H)+. 1H NMR (500 MHz, CDCl3): δ 8.21 (1H, d, J=1.9 Hz), 8.02 (1H, dd, J=8.5, 2.1 Hz), 7.63 (1H, d, J=7.5 Hz), 7.15 (1H, d, J=7.6 Hz), 7.13 (1H, d, J=8.7 Hz), 7.04 (1H, br s), 6.96 (2H, J=8.5 Hz), 6.90 (1H, d, J=8.6 Hz), 4.65-4.95 (2H, br), 2.67 (3H, s), 1.26 (9H, s).

Workup

  1. customThe volatiles were removed
  2. customthe residue was chromatographed on a SiO2 column
  3. customto provide acetyl product, which
  4. stirringwas stirred at 80° C. for 3 h
  5. customThe volatiles were removed
  6. customthe residue was purified by SiO2 column chromatography

Sources & evidence

ORD record
ord-90b1ccc80c784d04a9fac02305182f77
Source dataset
uspto-grants-2012_04
Patent number
US08153626B2

Reaction notes

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