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

HRID 1512702Notes

Reaction equation

HRID 1512702 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.Cl.Cl.[NH2:32][C:33]1[C:41]([NH2:42])=[CH:40][CH:39]=[CH:38][C:34]=1[C:35]([NH2:37])=[O:36].N>N1C=CC=CC=1.CN(C=O)C>[NH2:32][C:33]1[C:34]([C:35]([NH2:37])=[O:36])=[CH:38][CH:39]=[CH:40][C:41]=1[NH:42][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

7

Reactant 4

HCID 222AmmoniaHCID 682631,1'-CarbonyldiimidazoleHCID 294936N-((Benzyloxy)carbonyl)-2-methylalanineHCID 534228072,3-Diaminobenzamide dihydrochloride

Product 1

HCID 68512848Benzyl 2-{[2-amino-3-(aminocarbonyl)phenyl]amino}-1,1-dimethyl-2-oxoethylcarbamate

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6228DimethylformamideSolvent

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 dihydrochloride (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

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

Sources & evidence

ORD record
ord-f3f3a3a79c3241adb0da397c6bef082a
Source dataset
uspto-grants-2012_07
Patent number
US08217070B2

Reaction notes

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