Triethylamine → HCID 57636508, compound

HRID 2110272Notes

Reaction equation

Cl.[NH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:17]=[C:16]3[C:12]([C:13]([NH:18][C:19]([C:21]4[CH:25]=[CH:24][S:23][CH:22]=4)=[O:20])=[N:14][NH:15]3)=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.C(N(CC)CC)C.[F:33][C:34]1[CH:39]=[CH:38][C:37]([C:40]([F:43])([F:42])[F:41])=[CH:36][C:35]=1[N:44]=[C:45]=[O:46]>O1CCCC1>[S:23]1[CH:24]=[CH:25][C:21]([C:19]([NH:18][C:13]2[C:12]3[C:16](=[CH:17][C:9]([C:6]4[CH:5]=[CH:4][C:3]([NH:2][C:45]([NH:44][C:35]5[CH:36]=[C:37]([C:40]([F:41])([F:43])[F:42])[CH:38]=[CH:39][C:34]=5[F:33])=[O:46])=[CH:8][CH:7]=4)=[CH:10][CH:11]=3)[NH:15][N:14]=2)=[O:20])=[CH:22]1

Participants

Conditions

Temperature: 24 °C

Procedure

A solution of 1.72 g of 6-(4-aminophenyl)-3-[(thiophen-3-yl)carbonylamino]-1H-indazole hydrochloride and 0.65 mL of triethylamine in 70 mL of tetrahydrofuran is admixed slowly under an argon atmosphere with 0.67 mL of 2-fluoro-5-trifluoromethylphenyl isocyanate. The reaction mixture is stirred at 24° C. for 3.5 hours and then concentrated under reduced pressure. The residue is purified by flash chromatography on a silica column (60; 35-70 μM), eluting with a dichloromethane/methanol (97/3 by volume) mixture, to give 0.4 g of 1-(4-{3-[(thiophen-3-yl)carbonylamino]-1H-indazol-6-yl}phenyl)-3-(2-fluoro-5-trifluoromethylphenyl)urea, whose characteristics are as follows:

Workup

concentrationconcentrated under reduced pressure
customThe residue is purified by flash chromatography on a silica column (60; 35-70 μM)
washeluting with a dichloromethane/methanol (97/3 by volume) mixture

Sources & evidence

ORD record: ord-f28241a8663143f7b3e6f0c975f76e07
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07517902B2

Reaction notes

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