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Triethylamine → N-[5-(3,5-difluoro-benzenesulfonyl)-1H-indazol-3-yl]-4-(4-methyl-piperazin-1-yl)-2-(tetrahydro-pyran-4-ylamino)-benzamide

HRID 1640992
Notes
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Reaction equation

HRID 1640992 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([S:9]([C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[NH:17][N:16]=[C:15]3[NH:21][C:22](=[O:49])[C:23]2[CH:28]=[CH:27][C:26]([N:29]3[CH2:34][CH2:33][N:32]([CH3:35])[CH2:31][CH2:30]3)=[CH:25][C:24]=2[N:36]([CH:43]2[CH2:48][CH2:47][O:46][CH2:45][CH2:44]2)C(=O)C(F)(F)F)(=[O:11])=[O:10])[CH:5]=[C:6]([F:8])[CH:7]=1.C(N(CC)CC)C>CO>[F:1][C:2]1[CH:3]=[C:4]([S:9]([C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[NH:17][N:16]=[C:15]3[NH:21][C:22](=[O:49])[C:23]2[CH:28]=[CH:27][C:26]([N:29]3[CH2:30][CH2:31][N:32]([CH3:35])[CH2:33][CH2:34]3)=[CH:25][C:24]=2[NH:36][CH:43]2[CH2:48][CH2:47][O:46][CH2:45][CH2:44]2)(=[O:10])=[O:11])[CH:5]=[C:6]([F:8])[CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 86643844N-[5-(3,5-difluoro-benzenesulfonyl)-1H-indazol-3-yl]-4-(4-methyl-piperazin-1-yl)-2-[(tetrahydro-pyran-4-yl)-(2,2,2-trifluoro-acetyl)-amino]-benzamide

Product 1

HCID 59437080N-[5-(3,5-difluoro-benzenesulfonyl)-1H-indazol-3-yl]-4-(4-methyl-piperazin-1-yl)-2-(tetrahydro-pyran-4-ylamino)-benzamideYield 81.9%

Reagents, catalysts & solvents 1

HCID 887
Methanol
Solvent

Procedure

A mixture of N-[5-(3,5-difluoro-benzenesulfonyl)-1H-indazol-3-yl]-4-(4-methyl-piperazin-1-yl)-2-[(tetrahydro-pyran-4-yl)-(2,2,2-trifluoro-acetyl)-amino]-benzamide (1.41 g, 2.0 mmol), triethylamine (5.6 mL) and methanol (30 mL) was stirred at room temperature overnight. The solvents were removed under reduced pressure and the residue treated with methanol (10 mL), stirred at 45° C. for 30 minutes, filtered and dried in oven affording 1.0 g of the title compound as a white solid (81% yield).

Workup

  1. customThe solvents were removed under reduced pressure
  2. additionthe residue treated with methanol (10 mL)
  3. stirringstirred at 45° C. for 30 minutes
  4. filtrationfiltered
  5. customdried in oven

Sources & evidence

ORD record
ord-c03d247b12c5430ca7131ce17bfd9f46
Source dataset
uspto-grants-2012_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08114865B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes