Ammonia → HCID 58976032, compound

HRID 601047Notes

Reaction equation

HRID 601047 reaction equation
C(N1C=CN=C1)([N:3]1C=CN=C1)=O.[NH2:13][C:14]1[N:18]([C:19]2[CH:27]=[CH:26][C:22]([C:23](O)=[O:24])=[CH:21][CH:20]=2)[N:17]=[C:16]([NH:28][C:29]2[CH:34]=[C:33]([O:35][CH3:36])[C:32]([O:37][CH3:38])=[C:31]([O:39][CH3:40])[CH:30]=2)[N:15]=1.N>CN(C=O)C>[NH2:13][C:14]1[N:18]([C:19]2[CH:20]=[CH:21][C:22]([C:23]([NH2:3])=[O:24])=[CH:26][CH:27]=2)[N:17]=[C:16]([NH:28][C:29]2[CH:34]=[C:33]([O:35][CH3:36])[C:32]([O:37][CH3:38])=[C:31]([O:39][CH3:40])[CH:30]=2)[N:15]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 682631,1'-CarbonyldiimidazoleHCID 58977026HCID 58977026, compound

Product 1

HCID 58976032HCID 58976032, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0° C., 1,1′-carbonyldiimidazole (83 mg, 0.5 mmol) was added to a solution of 4-[5-amino-3-(3,4,5-trimethoxy-phenylamino)-[1,2,4]triazol-1-yl]-benzoic acid (100 mg, 0.25 mmol) in DMF (3 mL). The reaction mixture was stirred at rt. for 1 h, and ammonia (7.0M in MeOH, 1 mL) was added. The reaction mixture was stirred at rt. for 2 days. The mixture was then purified by semi-prep HPLC. FIA-MS: m/e=385.1 (M+H), 383.1 (ES−). Rt=3.60 min (method A). 1H-NMR (500 MHz, DMSO(d6)): 8.87 (s, 1H), 8.02 (br.s, 1H), 7.99 (d, 2H), 7.67 (d, 2H), 7.39 (br.s, 1H), 7.00 (s, 2H), 6.62 (s, 2H), 3.78 (s, 6H), 3.65 (s, 3H).

Workup

  1. stirringThe reaction mixture was stirred at rt
  2. waitfor 2 days
  3. customThe mixture was then purified by semi-prep HPLC

Sources & evidence

ORD record
ord-b46c2a15432046eb8df6efb40e06eb7c
Source dataset
uspto-grants-2011_03
Patent number
US07902239B2

Reaction notes

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