[4-(6,6-Dimethyl-5,6,7,8-tetrahydroquinazolin-4-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl]boronic acid → 4-(6,6-dimethyl-5,6,7,8-tetrahydroquinazolin-4-yl)-7-(1H-imidazo[4,5-b]pyridin-6-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepine

HRID 241108Notes

Reaction equation

HRID 241108 reaction equation
Br[C:2]1[CH:3]=[C:4]2[N:10](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:9]=[N:8][C:5]2=[N:6][CH:7]=1.[CH3:30][C:31]1([CH3:55])[CH2:40][CH2:39][C:38]2[N:37]=[CH:36][N:35]=[C:34]([N:41]3[CH2:47][C:46]4[CH:48]=[C:49](B(O)O)[CH:50]=[CH:51][C:45]=4[O:44][CH2:43][CH2:42]3)[C:33]=2[CH2:32]1>>[CH3:30][C:31]1([CH3:55])[CH2:40][CH2:39][C:38]2[N:37]=[CH:36][N:35]=[C:34]([N:41]3[CH2:47][C:46]4[CH:48]=[C:49]([C:2]5[CH:3]=[C:4]6[NH:10][CH:9]=[N:8][C:5]6=[N:6][CH:7]=5)[CH:50]=[CH:51][C:45]=4[O:44][CH2:43][CH2:42]3)[C:33]=2[CH2:32]1

Participants

3

Reactant 2

HCID 66820411[4-(6,6-Dimethyl-5,6,7,8-tetrahydroquinazolin-4-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl]boronic acidHCID 668205796-bromo-1-(triphenylmethyl)-1H-imidazo[4,5-b]pyridine

Product 1

HCID 595863994-(6,6-dimethyl-5,6,7,8-tetrahydroquinazolin-4-yl)-7-(1H-imidazo[4,5-b]pyridin-6-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepine

Procedure

Prepared according to the method of example 5 by using 6-bromo-1-(triphenylmethyl)-1H-imidazo[4,5-b]pyridine (reagent preparation 15) 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): 8.64 (s, 1H), 8.48 (s, 1H), 8.39 (s, 1H), 8.22 (brs, 1H), 7.75 (d, 1H), 7.58 (dd, 1H), 7.06 (d, 1H), 4.67 (s, 2H), 4.35 (m, 2H), 3.85 (m, 2H), 2.72 (m, 2H), 2.46 (s, 2H), 1.61 (m, 2H), 0.85 (s, 6H); MS (EI) for C25H26N6O: 427 (MH+).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-7659bccf73e6413e87041c7b68722c7a
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

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