Aniline → 5-Methyl-thiazole-2-carboxylic acid {3-(3-styryl-1H-indazol-6-yloxy)-phenyl]-amide
Reaction equation
C1(N)C=CC=CC=1.CC1SC(C([N:16]2[C:24]3[C:19](=[CH:20][CH:21]=[C:22]([O:25][C:26]4[CH:27]=[C:28]([NH:32][C:33]([C:35]5[S:36][C:37]([CH3:40])=[CH:38][N:39]=5)=[O:34])[CH:29]=[CH:30][CH:31]=4)[CH:23]=3)[C:18]([CH:41]=[CH:42][C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)=[N:17]2)=O)=NC=1.CC1SC(C(O)=O)=NC=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>CN(C=O)C>[CH:41]([C:18]1[C:19]2[C:24](=[CH:23][C:22]([O:25][C:26]3[CH:27]=[C:28]([NH:32][C:33]([C:35]4[S:36][C:37]([CH3:40])=[CH:38][N:39]=4)=[O:34])[CH:29]=[CH:30][CH:31]=3)=[CH:21][CH:20]=2)[NH:16][N:17]=1)=[CH:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1Participants
7
Reactant 5
HCID 6115Aniline
HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinone
HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)
HCID 218773495-Methyl-1,3-thiazole-2-carboxylic acid
HCID 695953325-Methyl-thiazole-2-carboxylic acid{3-[1-(5-methyl-thiazole-2-carbonyl)-3-styryl-1h-indazol-6-yloxy]-phenyl}amideProduct 1
Reagents, catalysts & solvents 1
Procedure
3-3-Styryl-4,5-dihydro-1H-indazol-6-yloxy)-phenylamine was converted to 5-methyl-thiazole-2-carboxylic acid {3-[1-(5-methyl-thiazole-2-carbonyl)-3-styryl-1H-indazol-6-yloxy]-phenyl}amide by treatment with 5-methyl-thiazole-2-carboxylic acid and HATU (o-(2-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate) in DMF and analogous work-up, DDQ treatment and isolation to Example 4(a), step (iv) (50% yield): 1H NMR (DMSO-d6) δ 10.85 (s, 1H), 8.45 (d, 1H, J=9.8 Hz), 8.24 (m, 3H), 7.99-7.62 (m, 6H), 7.54-7.34 (m, 5H), 6.96 (d, 1H, J=8.5 Hz), 2.64 (s, 3H), 2.54 (s, 3H).
Sources & evidence
- ORD record
- ord-859d254ece3a42409c773404b9bdd944
- Source dataset
- uspto-grants-2005_05
- Patent number
- US06891044B2
Reaction notes
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