2-methyl-1H-indol-5-ol → {4-Methyl-2-[7-(2-methyl-1H-indol-5-yloxy)-thieno[3,2-b]pyridin-2-yl]-thiazol-5-yl}-(4-methyl-piperazin-1-yl)-methanone

HRID 889900Notes

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

Participants

Reactant 2

HCID 833362-methyl-1H-indol-5-ol

HCID 22250086HCID 22250086, compound

Product 1

HCID 10141934{4-Methyl-2-[7-(2-methyl-1H-indol-5-yloxy)-thieno[3,2-b]pyridin-2-yl]-thiazol-5-yl}-(4-methyl-piperazin-1-yl)-methanoneYield 51%

Procedure

The title compound (77 mg, 51%) 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 2-methyl-1H-indol-5-ol by a procedure analogous to Example 16 as a tan colored hydrochloride salt. C26H25N5O2S2: APCI m/z 504.3 (pos.); 1H NMR (CD3OD): δ 8.46 (d, 1H, J=5.4 Hz), 7.99 (s, 1H), 7.35 (d, 1H, J=8.3 Hz), 7.26 (s, 1H), 6.87 (d, 1H, J=8.3 Hz), 6.67 (d, 1H, J=5.4 Hz), 6.17 (s, 1H), 3.8–3.0 (bm, 8H), 2.95 (s, 3H), 2.49 (s, 3H), 2.43 (s, 3H) ppm.

Sources & evidence

ORD record: ord-f4bb3839b54c42eb9ad597d909b57323
Source dataset: uspto-grants-2006_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06995171B2

Reaction notes

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