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

HRID 241119Notes

Reaction equation

HRID 241119 reaction equation
C1(COC(=O)[N:10]([CH2:12][C:13]2[N:22](COCC[Si](C)(C)C)[C:16]3=[N:17][CH:18]=[C:19](Br)[CH:20]=[C:15]3[N:14]=2)[CH3:11])C=CC=CC=1.[CH3:32][C:33]1([CH3:57])[CH2:42][CH2:41][C:40]2[N:39]=[CH:38][N:37]=[C:36]([N:43]3[CH2:49][C:48]4[CH:50]=[C:51](B(O)O)[CH:52]=[CH:53][C:47]=4[O:46][CH2:45][CH2:44]3)[C:35]=2[CH2:34]1>>[CH3:32][C:33]1([CH3:57])[CH2:42][CH2:41][C:40]2[N:39]=[CH:38][N:37]=[C:36]([N:43]3[CH2:49][C:48]4[CH:50]=[C:51]([C:19]5[CH:20]=[C:15]6[NH:14][C:13]([CH2:12][NH:10][CH3:11])=[N:22][C:16]6=[N:17][CH:18]=5)[CH:52]=[CH:53][C:47]=4[O:46][CH2:45][CH2:44]3)[C:35]=2[CH2:34]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 66820472phenylmethyl{[6-bromo-3-({[2-(trimethylsilyl)ethyl]oxy}methyl)-3H-imidazo[4,5-b]pyridin-2-yl]methyl}methylcarbamate

Product 1

HCID 595864601-{6-[4-(6,6-dimethyl-5,6,7,8-tetrahydroquinazolin-4-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl]-1H-imidazo[4,5-b]pyridin-2-yl}-N-methylmethanamine

Procedure

Prepared according to the method of example 5 by using phenylmethyl{[6-bromo-3-({[2-(trimethylsilyl)ethyl]oxy}methyl)-3H-imidazo[4,5-b]pyridin-2-yl]methyl}methylcarbamate (reagent preparation 19) 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, Methanol-d4): 8.62 (br, 1H), 8.35 (s, 1H), 8.10 (s, 1H), 7.62 (br, 1H), 7.53 (d, 1H), 7.09 (d, 1H), 4.74 (s, 2H), 4.38 (m, 2H), 4.22 (s, 2H), 3.97 (m, 2H), 2.77 (t, 2H), 2.59 (s, 3H), 2.48 (s, 2H), 1.68 (t, 2H), 0.88 (s, 6H); MS (EI) for C27H31N7O: 470 (MH+).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-6a7a71f7c4eb465cae30c7216a486168
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

Loading…