Triethylamine → HCID 86760168, compound
Reaction equation
[F:1][C:2]1[CH:10]=[C:9]([C:11]2[N:15]3[CH:16]=[C:17]([C:20]4[C:21](C)=[N:22][N:23]([C:25]([C:38]5[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=5)([C:32]5[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=5)[C:26]5[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=5)[CH:24]=4)[CH:18]=[CH:19][C:14]3=[N:13][CH:12]=2)[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[NH2:45][C:46]1[S:47][CH:48]=[C:49]([CH3:51])[N:50]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=C[C:62]=2N=N1.C(N(CC)CC)C>ClCCl>[CH3:51][C:49]1[N:50]=[C:46]([NH:45][C:4](=[O:6])[C:3]2[CH:7]=[CH:8][C:9]([C:11]3[N:15]4[CH:16]=[C:17]([C:20]5[CH:21]=[N:22][N:23]([C:25]([C:32]6[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=6)([C:38]6[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=6)[C:26]6[CH:31]=[CH:30][CH:29]=[C:28]([CH3:62])[CH:27]=6)[CH:24]=5)[CH:18]=[CH:19][C:14]4=[N:13][CH:12]=3)=[CH:10][C:2]=2[F:1])[S:47][CH:48]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
58 mg 2-fluoro-4-[6-(3-methyl-1-trityl-1H-4-pyrazolyl)imidazo[1,2-a]pyridin-3-yl] benzoic acid (compound in Example 470) and 13 mg 2-amino-4-methyl-1,3-thiazole were allowed to react for 12 hours with 49 mg benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate and 17 μL triethylamine in 2 mL dichloromethane. The reaction solution was purified by an NH silica gel column to give 59 mg N1-(4-methyl-1,3-thiazol-2-yl)-2-fluoro-4-[6-(3-methyl-trityl-1H-4-pyrazolyl)imidazo[1,2-a]pyridin-3-yl] benzamide as colorless crystals. This product was subjected to deprotection of the trityl group by the same method as in Example 68, to give 42 mg of the title compound as pale yellow crystals.
Workup
- customThe reaction solution was purified by an NH silica gel column
Sources & evidence
- ORD record
- ord-ff3c37d2af3f4333a06c18d7b79da3ed
- Source dataset
- uspto-grants-2006_07
- Patent number
- US07074801B1
Reaction notes
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