(1-Methyl-1H-indazol-7-yl)boronic acid → HCID 178481734, compound

HRID 389581Notes

Reaction equation

HRID 389581 reaction equation
C([Si](C)(C)[O:6][CH:7]1[CH2:12][CH2:11][CH:10]([N:13]2[CH:17]=[C:16]([C:18]3[CH:23]=[N:22][C:21]([NH2:24])=[C:20]4[O:25][C:26](Cl)=[CH:27][C:19]=34)[CH:15]=[N:14]2)[CH2:9][CH2:8]1)(C)(C)C.[CH3:31][N:32]1[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][C:39]=2B(O)O)[CH:34]=[N:33]1>>[NH2:24][C:21]1[N:22]=[CH:23][C:18]([C:16]2[CH:15]=[N:14][N:13]([C@H:10]3[CH2:9][CH2:8][C@H:7]([OH:6])[CH2:12][CH2:11]3)[CH:17]=2)=[C:19]2[CH:27]=[C:26]([C:39]3[CH:38]=[CH:37][CH:36]=[C:35]4[C:40]=3[N:32]([CH3:31])[N:33]=[CH:34]4)[O:25][C:20]=12

Participants

3

Reactant 2

HCID 44118216(1-Methyl-1H-indazol-7-yl)boronic acidHCID 667601224-{1-[4-(tert-butyldimethyl-silanyloxy)-cyclohexyl]-1H-pyrazol-4-yl}-2-chlorofuro[2,3-c]pyridin-7-ylamine

Product 1

HCID 178481734HCID 178481734, compoundYield 69%

Procedure

The title compound was prepared in 69% yield from 4-{1-[4-(tert-butyldimethyl-silanyloxy)-cyclohexyl]-1H-pyrazol-4-yl}-2-chlorofuro[2,3-c]pyridin-7-ylamine and 1-methylindazole-7-boronic acid by a procedure analogous to Example 229. The material was further purified by preparative TLC (5% 7 N ammonia/MeOH:ethyl acetate) instead of trituration. 1H NMR (400 MHz, DMSO-d6): δ 8.24 (s, 1H), 8.23 (s, 1H), 8.03 (s, 1H), 7.98 (dd, J=0.76, 8.08 Hz, 1H), 7.92 (s, 1H), 7.71 (dd, J=1.01, 7.07 Hz, 1H), 7.56 (s, 1H), 7.29 (dd, J=7.20, 7.96 Hz, 1H), 6.41 (br s, 2H), 4.67 (d, J=4.29 Hz, 1H), 4.15 (tt, J=3.95, 11.59 Hz, 1H), 3.91 (s, 3H), 3.46-3.57 (m, 1H), 2.04 (d, J=12.13 Hz, 2H), 1.79-1.98 (m, 4H), 1.30-1.43 (m, 2H); MS (ESI): 428.94 [M+H]+; HPLC tR=2.63 min (ZQ3: polar—5 min).

Workup

  1. customThe material was further purified by preparative TLC (5% 7 N ammonia/MeOH:ethyl acetate) instead of trituration
  2. customHPLC tR=2.63 min (ZQ3: polar—5 min)

Sources & evidence

ORD record
ord-dcc30ba66d9847529a6bfb81ce03d3db
Source dataset
uspto-grants-2013_02
Patent number
US08378104B2

Reaction notes

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