Ammonia → Benzyl 2-{[2-amino-3-(aminocarbonyl)phenyl]amino}-1,1-dimethyl-2-oxoethylcarbamate

HRID 12630

Reaction equation

[CH2:1]([O:8][C:9]([NH:11][C:12]([CH3:17])([CH3:16])[C:13]([OH:15])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:30][C:31]1[C:39]([NH2:40])=[CH:38][CH:37]=[CH:36][C:32]=1[C:33]([NH2:35])=[O:34].N>N1C=CC=CC=1.CN(C=O)C>[NH2:30][C:31]1[C:32]([C:33]([NH2:35])=[O:34])=[CH:36][CH:37]=[CH:38][C:39]=1[NH:40][C:13](=[O:15])[C:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)([CH3:17])[CH3:16]

Participants

Conditions

Temperature: 40 °C

Procedure

2-{[(Benzyloxy)carbonyl]amino}-2-methylpropanoic acid (5.18 g, 21.83 mmol) in a mixture of pyridine (25 mL) and DMF (25 mL) was treated with 1,1′-carbonyldiimidazole (3.72 g, 22.92 mmol) and heated at 40° C. for 2 hours. 2,3-Diaminobenzamide dihydrochlolide (4.89 g, 21.83 mmol), prepared as described in WO0026192, was added and the mixture was stirred at room temperature overnight. The solvents were removed under vacuum and the residue was partitioned between ethyl acetate and diluted sodium bicarbonate aqueous solution. The formed slightly yellow solid material was collected by filtration, washed with water and ethyl acetate, and dried to give Example 1A. MS (DCI/NH3) m/z 371 (M+H)+.

Workup

additionwas added
customThe solvents were removed under vacuum
customthe residue was partitioned between ethyl acetate and diluted sodium bicarbonate aqueous solution
customThe formed slightly yellow solid material
filtrationwas collected by filtration
washwashed with water and ethyl acetate
customdried
customto give Example 1A

Sources & evidence

ORD record: ord-9c25fc59113f4ee5ad6fdc1b8bb23676
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07728026B2

Linked notes

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