Ammonia → HCID 21083995, compound

HRID 347934Notes

Reaction equation

HRID 347934 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:13](=[O:14])[CH:12]=[CH:11][C:10]2[C:15]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[C:16]([C:18](O)=[O:19])[S:17][C:9]1=2.C(N1C=CN=C1)([N:29]1C=CN=C1)=O.N>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:13](=[O:14])[CH:12]=[CH:11][C:10]2[C:15]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[C:16]([C:18]([NH2:29])=[O:19])[S:17][C:9]1=2

Participants

5

Reactant 3

HCID 222AmmoniaHCID 682631,1'-CarbonyldiimidazoleHCID 21083996HCID 21083996, compound

Product 1

HCID 21083995HCID 21083995, compoundYield 84.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of the compound of Example 126 (125 mg, 0.328 mmol) and 1,1′-carbonyldiimidazole (80 mg, 0.49 mmol) in DMF (3 mL) was stirred at r.t. for 90 min. Concentrated ammonia solution (0.5 mL) was added and the mixture stirred for 1 h. Volatiles were removed in vacuo. The residue was treated with 2M HCl(aq) and the resulting solid filtered off and dried. Purification by column chromatography on silica (3% MeOH in DCM) gave the title compound as a pale brown solid (105 mg, 84%). δH (DMSO-d6) 7.91–7.89 (1H, m), 7.83–7.80 (1H, m), 7.76–7.69 (2H, m), 7.66–7.59 (3H, m), 7.56–7.53 (2H, m), 7.51 (1H, d, J 9.7 Hz), 6.62 (1H, d, J 9.6 Hz), 6.2 (2H, br s). LCMS (ES+) RT 3.120 minutes, 380.8 (M+H)+.

Workup

  1. stirringthe mixture stirred for 1 h
  2. customVolatiles were removed in vacuo
  3. additionThe residue was treated with 2M HCl(aq)
  4. filtrationthe resulting solid filtered off
  5. customdried
  6. customPurification by column chromatography on silica (3% MeOH in DCM)

Sources & evidence

ORD record
ord-cecd747775cd4cf19aadaa0d66d833c0
Source dataset
uspto-grants-2007_02
Patent number
US07176215B2

Reaction notes

Loading…