Acetic Anhydride → 3-[2-chloro-5-(2,3,4,5-tetrahydro-benzo[b]azepine-1-sulfonyl)-phenyl]-2,6-dimethyl-3H-pyrimidin-4-one

HRID 2382703Notes

Reaction equation

HRID 2382703 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:17][CH2:16][CH2:15][CH2:14][C:13]3[CH:18]=[CH:19][CH:20]=[CH:21][C:12]2=3)(=[O:10])=[O:9])=[CH:4][C:3]=1[NH:22][C:23](=[O:28])[CH2:24][C:25](=[NH:27])[CH3:26].[C:29](OC(=O)C)(=O)[CH3:30]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:17][CH2:16][CH2:15][CH2:14][C:13]3[CH:18]=[CH:19][CH:20]=[CH:21][C:12]2=3)(=[O:9])=[O:10])=[CH:4][C:3]=1[N:22]1[C:23](=[O:28])[CH:24]=[C:25]([CH3:26])[N:27]=[C:29]1[CH3:30]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 86643504N-[2-chloro-5-(2,3,4,5-tetrahydro-benzo[b]azepine-1-sulfonyl)-phenyl]-3-imino-butyramide

Product 1

HCID 594102353-[2-chloro-5-(2,3,4,5-tetrahydro-benzo[b]azepine-1-sulfonyl)-phenyl]-2,6-dimethyl-3H-pyrimidin-4-one

Conditions

Temperature
85 °C

Procedure

To N-[2-chloro-5-(2,3,4,5-tetrahydro-benzo[b]azepine-1-sulfonyl)-phenyl]-3-imino-butyramide (42 mg, 0.1 mmol) in acetic anhydride (1 mL) was added 4-dimethyl-aminopyridine (6 mg, 0.1 mmol). The mixture was heated at 85° C. under stirring for 16 hrs. The mixture was then subjected to purification by prep. LCMS to afford 3-[2-chloro-5-(2,3,4,5-tetrahydro-benzo[b]azepine-1-sulfonyl)-phenyl]-2,6-dimethyl-3H-pyrimidin-4-one 14-1. MS: 443.8 (M+H)+; tR=6.94 min (method 2).

Workup

  1. customThe mixture was then subjected to purification by prep

Sources & evidence

ORD record
ord-cc599e0295ff496a8f272ec161d86836
Source dataset
uspto-grants-2012_09
Patent number
US08263588B2

Reaction notes

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