5-Hydroxy-2-methyl-1h-indole-3-carbonitrile → HCID 10165314, compound

HRID 889902Notes

Reaction equation

HRID 889902 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]3[S:12][C:13]([C:17]([N:19]4[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]4)=[O:18])=[C:14]([CH3:16])[N:15]=3)[S:10][C:3]=12.[OH:26][C:27]1[CH:28]=[C:29]2[C:33](=[CH:34][CH:35]=1)[NH:32][C:31]([CH3:36])=[C:30]2[C:37]#[N:38]>>[CH3:36][C:31]1[NH:32][C:33]2[C:29]([C:30]=1[C:37]#[N:38])=[CH:28][C:27]([O:26][C:2]1[CH:7]=[CH:6][N:5]=[C:4]3[CH:8]=[C:9]([C:11]4[S:12][C:13]([C:17]([N:19]5[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]5)=[O:18])=[C:14]([CH3:16])[N:15]=4)[S:10][C:3]=13)=[CH:35][CH:34]=2

Participants

3

Reactant 2

HCID 222500775-Hydroxy-2-methyl-1h-indole-3-carbonitrileHCID 22250086HCID 22250086, compound

Product 1

HCID 10165314HCID 10165314, compoundYield 41%

Procedure

The title compound (61 mg, 41%) was prepared from [2-(7-Chloro-thieno[3,2-b]pyridin-2-yl)-4-methyl-thiazol-5-yl]-(4-methyl-piperazin-1-yl)-methanone and 5-Hydroxy-2-methyl-1 H-indole-3-carbonitrile by a procedure analogous to Example 16 using and in a 41% yield. C27H25N6O2S2: APCI m/z 529.4 (pos.); 1H NMR (CD3OD): δ 8.72 (d, 1H, J=6.6 Hz), 8.17 (s, 1H), 7.60 (d, 1H, J=8.7 Hz), 7.58 (s, 1H), 7.23 (d, 1H, J=8.7 Hz), 7.07 (d, 1H, J=6.6 Hz), 3.65–3.15 (bm, 8H), 2.96 (s, 3H), 2.63 (s, 3H), 2.52 (s, 3H) ppm.

Sources & evidence

ORD record
ord-2cbfdd10cb9642f4bea03e9386e3f881
Source dataset
uspto-grants-2006_02
Patent number
US06995171B2

Reaction notes

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