2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 5-Methyl-thiazole-2-carboxylic acid {3-(3-styryl-1H-indazol-6-yloxy)-phenyl]-amide

HRID 724369Notes

Reaction equation

HRID 724369 reaction equation
C(C1C2CCC(OC3C=C(N)C=CC=3)=CC=2NN=1)=CC1C=CC=CC=1.CC1SC(C([N:34]2[C:42]3[C:37](=[CH:38][CH:39]=[C:40]([O:43][C:44]4[CH:45]=[C:46]([NH:50][C:51]([C:53]5[S:54][C:55]([CH3:58])=[CH:56][N:57]=5)=[O:52])[CH:47]=[CH:48][CH:49]=4)[CH:41]=3)[C:36]([CH:59]=[CH:60][C:61]3[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=3)=[N:35]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:59]([C:36]1[C:37]2[C:42](=[CH:41][C:40]([O:43][C:44]3[CH:45]=[C:46]([NH:50][C:51]([C:53]4[S:54][C:55]([CH3:58])=[CH:56][N:57]=4)=[O:52])[CH:47]=[CH:48][CH:49]=3)=[CH:39][CH:38]=2)[NH:34][N:35]=1)=[CH:60][C:61]1[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=1

Participants

7

Reactant 5

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 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 acidHCID 693704203-(3-Styryl-4,5-dihydro-1H-indazol-6-yloxy)-phenylamineHCID 695953325-Methyl-thiazole-2-carboxylic acid{3-[1-(5-methyl-thiazole-2-carbonyl)-3-styryl-1h-indazol-6-yloxy]-phenyl}amide

Product 1

HCID 865985405-Methyl-thiazole-2-carboxylic acid {3-(3-styryl-1H-indazol-6-yloxy)-phenyl]-amide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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 hexafluoro-phosphate) 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-c0b3c337275c45c49a2e3992d90034a7
Source dataset
uspto-grants-2006_11
Patent number
US07141587B2

Reaction notes

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