HCID 66759397, compound → 3-{4-[1-(1-acetylpiperidin-4-yl)-1H-pyrazol-4-yl]-7-aminofuro[2,3-c]pyridin-2-yl}-5-methylthieno[3,2-c]pyridin-6(5H)-one

HRID 389547Notes

Reaction equation

HRID 389547 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:12]2[CH:13]=[N:14][N:15]([CH:17]3[CH2:22][CH2:21][N:20]([C:23](=[O:25])[CH3:24])[CH2:19][CH2:18]3)[CH:16]=2)=[C:6]2[CH:10]=[C:9](Cl)[O:8][C:7]=12.[CH3:26][N:27]1[C:32](=[O:33])[CH:31]=[C:30]2[S:34][CH:35]=[C:36](B3OC(C)(C)C(C)(C)O3)[C:29]2=[CH:28]1>>[C:23]([N:20]1[CH2:21][CH2:22][CH:17]([N:15]2[CH:16]=[C:12]([C:5]3[CH:4]=[N:3][C:2]([NH2:1])=[C:7]4[O:8][C:9]([C:36]5[C:29]6=[CH:28][N:27]([CH3:26])[C:32](=[O:33])[CH:31]=[C:30]6[S:34][CH:35]=5)=[CH:10][C:6]=34)[CH:13]=[N:14]2)[CH2:18][CH2:19]1)(=[O:25])[CH3:24]

Participants

3

Reactant 2

HCID 66759397HCID 66759397, compoundHCID 667600985-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thieno[3,2-c]pyridin-6(5H)-one

Product 1

HCID 667604633-{4-[1-(1-acetylpiperidin-4-yl)-1H-pyrazol-4-yl]-7-aminofuro[2,3-c]pyridin-2-yl}-5-methylthieno[3,2-c]pyridin-6(5H)-oneYield 30%

Procedure

The title compound was prepared in 30% yield from 1-{4-[4-(7-amino-2-chlorofuro[2,3-c]pyridin-4-yl)-1H-pyrazol-1-yl]piperidin-1-yl}ethanone 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 223, Step D. 1H NMR (400 MHz, CD3OD): δ 9.01 (s, 1 H), 8.29 (s, 1 H), 8.17 (s, 1 H), 8.03 (s, 1 H), 7.83 (s, 1 H), 7.75 (s, 1 H), 7.07 (s, 1 H), 4.69 (m, J=13.1 Hz, 1 H), 4.51-4.62 (m, 1 H), 4.11 (m, J=16.4 Hz, 1 H), 3.87 (s, 3 H), 3.33-3.42 (m, 1 H), 2.80-2.96 (m, 1 H), 2.16-2.30 (m, 5 H), 1.95-2.15 (m, 2 H); MS (ESI): 489.37 [M+H]+; HPLC tR=2.32 min (ZQ3, polar—4 min).

Workup

  1. custom4 min

Sources & evidence

ORD record
ord-861058b233814c6f8a4a16c161098e0e
Source dataset
uspto-grants-2013_02
Patent number
US08378104B2

Reaction notes

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