Dimethylformamide dimethyl acetal → (S)-N-(3-bromophenyl)-N'-(N-((dimethylamino)methylene)sulfamoyl)-2-methyl-4-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperazine-1-carboximidamide

HRID 1892143Notes

Reaction equation

HRID 1892143 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]([N:15]2[CH2:20][CH2:19][N:18]([C:21]3[C:22]4[C:29]([CH3:30])=[CH:28][NH:27][C:23]=4[N:24]=[CH:25][N:26]=3)[CH2:17][C@@H:16]2[CH3:31])=[N:10][S:11](=[O:14])(=[O:13])[NH2:12])[CH:5]=[CH:6][CH:7]=1.CO[CH:34](OC)[N:35]([CH3:37])[CH3:36]>CO>[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]([N:15]2[CH2:20][CH2:19][N:18]([C:21]3[C:22]4[C:29]([CH3:30])=[CH:28][NH:27][C:23]=4[N:24]=[CH:25][N:26]=3)[CH2:17][C@@H:16]2[CH3:31])=[N:10][S:11](=[O:14])(=[O:13])[N:12]=[CH:34][N:35]([CH3:37])[CH3:36])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 68725919HCID 68725919, compound

Product 1

HCID 68963969(S)-N-(3-bromophenyl)-N'-(N-((dimethylamino)methylene)sulfamoyl)-2-methyl-4-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperazine-1-carboximidamideYield 13%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Crude (S)—N-(3-bromophenyl)-2-methyl-4-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-N′-sulfamoylpiperazine-1-carboximidamide from Example 20, step C, (˜25 mg, 0.068 mmol) was dissolved in MeOH (0.5 ml) and N,N-dimethylformamide dimethyl acetal (7 μl) added. The mixture was stirred at room temperature for 20 minutes and then concentrated. The mixture was purified by preparative HPLC to afford the desired compound (5 mg, 0.0088 mmol, 13%) as a white solid.

Workup

  1. concentrationconcentrated
  2. customThe mixture was purified by preparative HPLC

Sources & evidence

ORD record
ord-d0f5e4b927e24e0294221f91f57718a6
Source dataset
uspto-grants-2013_08
Patent number
US08507672B2

Reaction notes

Loading…