Ammonia → HCID 21083990, compound

HRID 347909Notes

Reaction equation

HRID 347909 reaction equation
C(N1C=CN=C1)([N:3]1C=CN=C1)=O.[O:13]=[C:14]1[N:19]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:18]2[S:26][C:27]([C:35]([OH:37])=O)=[C:28]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:17]=2[CH:16]=[CH:15]1.N>CN(C=O)C>[O:13]=[C:14]1[N:19]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:18]2[S:26][C:27]([C:35]([NH2:3])=[O:37])=[C:28]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:17]=2[CH:16]=[CH:15]1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 682631,1'-CarbonyldiimidazoleHCID 21083991HCID 21083991, compound

Product 1

HCID 21083990HCID 21083990, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1,1′-Carbonyidiimidazole (51 mg, 0.32 mmol) was added to the compound of Example 59 (100 mg, 0.29 mmol) in DMF (2 mL). After 15 min aq. ammonia (0.190 mL, 25% solution, 3.0 mmol) was added and the solution stirred at r.t. overnight. The mixture was concentrated in vacuo and azeotroped twice with heptane. The crude product was purified by column chromatography on silica (3% MeOH in DCM) to give the title compound as a white solid (74 mg, 74%). δH (DMSO-d6) 7.87–7.76 (3H, m), 7.75–7.68 (5H, m), 7.64–7.61 (2H, m), 7.54 (1H, d, J 9.6 Hz), 6.69 (1H, d, J 9.6 Hz), 6.25 (2H, br s). LCMS (ES+) RT 2.95 minutes, 347.0 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customazeotroped twice with heptane
  3. customThe crude product was purified by column chromatography on silica (3% MeOH in DCM)

Sources & evidence

ORD record
ord-07af6b97cd894741a997dd217a19a646
Source dataset
uspto-grants-2007_02
Patent number
US07176215B2

Reaction notes

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