Ammonia → HCID 21083997, compound

HRID 347933Notes

Reaction equation

HRID 347933 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[C:15](=[O:16])[CH:14]=[CH:13][C:12]2[C:17]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[C:18]([C:20]([OH:22])=O)[S:19][C:11]1=2)([O-:3])=[O:2].C(N1C=CN=C1)([N:31]1C=CN=C1)=O.N>CN(C=O)C>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[C:15](=[O:16])[CH:14]=[CH:13][C:12]2[C:17]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[C:18]([C:20]([NH2:31])=[O:22])[S:19][C:11]1=2)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 682631,1'-CarbonyldiimidazoleHCID 21083998HCID 21083998, compound

Product 1

HCID 21083997HCID 21083997, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of the compound of Example 123 (105 mg, 0.268 mmol) and 1,1′-carbonyldiimidazole (65 mg, 0.40 mmol) in DMF (3 mL) was stirred at r.t. for 45 min. Concentrated ammonia solution (1 mL) was added and the mixture stirred overnight at r.t. Volatiles were removed in vacuo, the residue taken up in DCM, washed 2M HCl(aq), dried (Na2SO4), and concentrated in vacuo. Purification by column chromatography on silica (4% MeOH in DCM) gave the title compound as a yellow solid (42 mg). δH (DMSO-d6) 8.28 (1H, dd, J 1.3, 8.2 Hz), 7.99 (1H, dt, J 1.4, 7.8 Hz), 7.92 (1H, dd, J 1.4, 7.8 Hz), 7.87–7.82 (1H, m), 7.54–7.47 (3H, m), 7.46–7.37 (3H, m), 6.44 (1H, d, J 9.7 Hz), 6.21 (2H, v br). LCMS (ES+) RT 2.997 minutes, 392.0 (M+H)+.

Workup

  1. stirringthe mixture stirred overnight at r.t
  2. customVolatiles were removed in vacuo
  3. washwashed 2M HCl(aq)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customPurification by column chromatography on silica (4% MeOH in DCM)

Sources & evidence

ORD record
ord-44be8d59ef3144559d970114e9785288
Source dataset
uspto-grants-2007_02
Patent number
US07176215B2

Reaction notes

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