HCID 66759397, compound → 5-{4-[1-(1-acetylpiperidin-4-yl)-1H-pyrazol-4-yl]-7-aminofuro[2,3-c]pyridin-2-yl}-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-3-carbonitrile

HRID 389518Notes

Reaction equation

HRID 389518 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.[O:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH:27]1[N:32]1[C:40]2[C:35](=[CH:36][C:37](B3OC(C)(C)C(C)(C)O3)=[CH:38][CH:39]=2)[C:34]([C:50]#[N:51])=[N:33]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:37]5[CH:36]=[C:35]6[C:40](=[CH:39][CH:38]=5)[N:32]([CH:27]5[CH2:28][CH2:29][CH2:30][CH2:31][O:26]5)[N:33]=[C:34]6[C:50]#[N:51])=[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 667594851-(tetrahydro-2H-pyran-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole-3-carbonitrile

Product 1

HCID 667597385-{4-[1-(1-acetylpiperidin-4-yl)-1H-pyrazol-4-yl]-7-aminofuro[2,3-c]pyridin-2-yl}-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-3-carbonitrileYield 65%

Procedure

The title compound was prepared in 65% yield from 1-{4-[4-(7-amino-2-chlorofuro[2,3-c]pyridin-4-yl)-1H-pyrazol-1-yl]piperidin-1-yl}ethanone and 1-(tetrahydro-2H-pyran-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole-3-carbonitrile by a procedure analogous to Example 87. 1H NMR (400 MHz, CDCl3): δ 8.39 (s, 1 H), 8.07-7.92 (m, 2 H), 7.90-7.80 (m, 2 H), 7.72 (s, 1 H), 7.19 (s, 1 H), 5.87 (dd, J=2.9, 8.2 Hz, 1 H), 4.97 (s, 2 H), 4.87-4.68 (m, 1 H), 4.60-4.28 (m, 1 H), 4.11-3.87 (m, 2 H), 3.88-3.68 (m, 1 H), 3.39-3.16 (m, 1 H), 2.95-2.69 (m, 1 H), 2.61-2.43 (m, 1 H), 2.31 (br. s, 2 H), 2.23-2.12 (m, 4 H), 2.12-1.96 (m, 2 H), 1.93-1.62 (m, 4 H); MS (ESI): 551.19 [M+H]+; HPLC tR=2.62 min (ZQ3, polar—4 min).

Workup

  1. custom4 min

Sources & evidence

ORD record
ord-56facf4b07244f20aa147b4749f47aac
Source dataset
uspto-grants-2013_02
Patent number
US08378104B2

Reaction notes

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