5-bromo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine → 4-(6,6-dimethyl-5,6,7,8-tetrahydroquinazolin-4-yl)-7-(1H-pyrazolo[3,4-b]pyridin-5-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepine

HRID 241107Notes

Reaction equation

HRID 241107 reaction equation
Br[C:2]1[CH:3]=[C:4]2[CH:10]=[N:9][N:8](C3CCCCO3)[C:5]2=[N:6][CH:7]=1.[CH3:17][C:18]1([CH3:42])[CH2:27][CH2:26][C:25]2[N:24]=[CH:23][N:22]=[C:21]([N:28]3[CH2:34][C:33]4[CH:35]=[C:36](B(O)O)[CH:37]=[CH:38][C:32]=4[O:31][CH2:30][CH2:29]3)[C:20]=2[CH2:19]1>>[CH3:17][C:18]1([CH3:42])[CH2:27][CH2:26][C:25]2[N:24]=[CH:23][N:22]=[C:21]([N:28]3[CH2:34][C:33]4[CH:35]=[C:36]([C:2]5[CH:3]=[C:4]6[CH:10]=[N:9][NH:8][C:5]6=[N:6][CH:7]=5)[CH:37]=[CH:38][C:32]=4[O:31][CH2:30][CH2:29]3)[C:20]=2[CH2:19]1

Participants

3

Reactant 2

HCID 583780645-bromo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridineHCID 66820411[4-(6,6-Dimethyl-5,6,7,8-tetrahydroquinazolin-4-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl]boronic acid

Product 1

HCID 687754124-(6,6-dimethyl-5,6,7,8-tetrahydroquinazolin-4-yl)-7-(1H-pyrazolo[3,4-b]pyridin-5-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepine

Procedure

Prepared according to the method of example 5 by using 5-bromo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine (reagent preparation 32) and [4-(6,6-dimethyl-5,6,7,8-tetrahydroquinazolin-4-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl]boronic acid (reagent preparation 23) in step 1. 1H NMR (400 MHz, d6-DMSO): 13.71 (s, 1H), 8.82 (d, 1H), 8.43 (d, 1H), 8.38 (s, 1H), 8.18 (d, 1H), 7.74 (d, 1H), 7.58 (dd, 1H), 7.07 (d, 1H), 4.66 (s, 2H), 4.34 (m, 2H), 3.85 (m, 2H), 2.71 (m, 2H), 2.45 (s, 2H), 1.59 (m, 2H), 0.84 (s, 6H); MS (EI) for C25H26N6O: 427 (MH+).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-2fe84df731894ace8172fa289a3f36d2
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

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