5-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thieno[3,2-c]pyridin-6(5H)-one → HCID 178479900, compound

HRID 389548Notes

Reaction equation

HRID 389548 reaction equation
[Si]([O:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([N:15]2[CH:19]=[C:18]([C:20]3[CH:25]=[N:24][C:23]([NH2:26])=[C:22]4[O:27][C:28](Cl)=[CH:29][C:21]=34)[CH:17]=[N:16]2)[CH2:11][CH2:10]1)(C(C)(C)C)(C)C.[CH3:31][N:32]1[C:37](=[O:38])[CH:36]=[C:35]2[S:39][CH:40]=[C:41](B3OC(C)(C)C(C)(C)O3)[C:34]2=[CH:33]1>>[NH2:26][C:23]1[N:24]=[CH:25][C:20]([C:18]2[CH:17]=[N:16][N:15]([C@H:12]3[CH2:13][CH2:14][C@H:9]([OH:8])[CH2:10][CH2:11]3)[CH:19]=2)=[C:21]2[CH:29]=[C:28]([C:41]3[C:34]4=[CH:33][N:32]([CH3:31])[C:37](=[O:38])[CH:36]=[C:35]4[S:39][CH:40]=3)[O:27][C:22]=12

Participants

3

Reactant 2

HCID 667600985-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thieno[3,2-c]pyridin-6(5H)-oneHCID 178455334HCID 178455334, compound

Product 1

HCID 178479900HCID 178479900, compoundYield 60%

Procedure

The title compound was prepared in 60% yield from 4-[1-(trans-4-{[tert-butyl(dimethyl)silyl]oxy}cyclohexyl)-1H-pyrazol-4-yl]-2-chlorofuro[2,3-c]pyridin-7-amine and 5-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thieno[3,2-c]pyridin-6(5H)-one by a procedure analogous to Example 229. 1H NMR (400 MHz, CD3OD): δ 8.98 (s, 1 H), 8.11 (s, 1 H), 7.99-8.03 (m, 1 H), 7.87-7.95 (m, 2 H), 7.43-7.52 (m, 1 H), 6.96-7.10 (m, 1 H), 4.16-4.37 (m, 1 H), 3.88 (s, 3 H), 3.61-3.78 (m, 1 H), 1.85-2.31 (m, 6 H), 1.39-1.69 (m, 2 H); MS (ESI): 462.28 [M+H]+; HPLC tR=2.30 min (ZQ3, polar—4 min).

Workup

  1. custom4 min

Sources & evidence

ORD record
ord-55992b5c895b4ff5a9d762cfe5832a0b
Source dataset
uspto-grants-2013_02
Patent number
US08378104B2

Reaction notes

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