Pyrrole-2-carbonyl chloride → HCID 46244579, compound

HRID 1803851Notes

Reaction equation

HRID 1803851 reaction equation
[NH2:1][C:2]1[CH:29]=[C:28]([N:30]([CH2:32][CH2:33][CH2:34][N:35]([CH3:37])[CH3:36])[CH3:31])[CH:27]=[CH:26][C:3]=1[C:4]([NH:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:16][CH2:17][C:18]3[CH:23]=[C:22]([F:24])[CH:21]=[C:20]([F:25])[CH:19]=3)[CH:14]=2)[NH:9][N:8]=1)=[O:5].[NH:38]1[CH:42]=[CH:41][CH:40]=[C:39]1[C:43](Cl)=[O:44]>N1C=CC=CC=1>[F:24][C:22]1[CH:23]=[C:18]([CH:19]=[C:20]([F:25])[CH:21]=1)[CH2:17][O:16][C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][CH:12]=1)[NH:9][N:8]=[C:7]2[NH:6][C:4]([C:3]1[CH:26]=[CH:27][C:28]([N:30]([CH2:32][CH2:33][CH2:34][N:35]([CH3:36])[CH3:37])[CH3:31])=[CH:29][C:2]=1[NH:1][C:43]([C:39]1[NH:38][CH:42]=[CH:41][CH:40]=1)=[O:44])=[O:5]

Participants

4

Reactant 2

HCID 224558Pyrrole-2-carbonyl chlorideHCID 46244400HCID 46244400, compound

Product 1

HCID 46244579HCID 46244579, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-Amino-N-[5-(3,5-difluoro-benzyloxy)-1H-indazol-3-yl]-4-[(3-dimethylamino-propyl)-methyl-amino]-benzamide (115 mg, 0.23 mmol) in pyridine (2.2 mL), cooled to 4° C., was treated with solid 1H-pyrrole-2-carbonyl chloride (34 mg, 0.27 mmol). The reaction was stirred until clear and left to room temperature over night. After removal of the volatiles, the crude was purified over silica gel to afford 90 mg of title compound in 66% yield.

Workup

  1. waitleft to room temperature over night
  2. customAfter removal of the volatiles
  3. customthe crude was purified over silica gel

Sources & evidence

ORD record
ord-1c91f8fbff75405c9d1097175bd90bb1
Source dataset
uspto-grants-2013_01
Patent number
US08354399B2

Reaction notes

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