[4-(6,6-Dimethyl-5,6,7,8-tetrahydroquinazolin-4-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl]boronic acid → phenylmethyl[(1S)-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}ethyl]carbamate

HRID 241121Notes

Reaction equation

HRID 241121 reaction equation
[C:1]1([CH2:7][O:8][C:9](=[O:39])[N:10]([C@H:19]([C:21]2[N:30](COCC[Si](C)(C)C)[C:24]3=[N:25][CH:26]=[C:27](Br)[CH:28]=[C:23]3[N:22]=2)[CH3:20])COCC[Si](C)(C)C)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:40][C:41]1([CH3:65])[CH2:50][CH2:49][C:48]2[N:47]=[CH:46][N:45]=[C:44]([N:51]3[CH2:57][C:56]4[CH:58]=[C:59](B(O)O)[CH:60]=[CH:61][C:55]=4[O:54][CH2:53][CH2:52]3)[C:43]=2[CH2:42]1>>[C:1]1([CH2:7][O:8][C:9](=[O:39])[NH:10][C@H:19]([C:21]2[NH:22][C:23]3[C:24]([N:30]=2)=[N:25][CH:26]=[C:27]([C:59]2[CH:60]=[CH:61][C:55]4[O:54][CH2:53][CH2:52][N:51]([C:44]5[C:43]6[CH2:42][C:41]([CH3:40])([CH3:65])[CH2:50][CH2:49][C:48]=6[N:47]=[CH:46][N:45]=5)[CH2:57][C:56]=4[CH:58]=2)[CH:28]=3)[CH3:20])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=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 68772361phenylmethyl{(1S)-1-[6-bromo-3-({[2-(trimethylsilyl)ethyl]oxy}methyl)-3H-imidazo[4,5-b]pyridin-2-yl]ethyl}({[2-(trimethylsilyl)ethyl]oxy}methyl)carbamate

Product 1

HCID 59586644phenylmethyl[(1S)-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}ethyl]carbamate

Procedure

Prepared according to the method of example 5 by using phenylmethyl{(1S)-1-[6-bromo-3-({[2-(trimethylsilyl)ethyl]oxy}methyl)-3H-imidazo[4,5-b]pyridin-2-yl]ethyl}({[2-(trimethylsilyl)ethyl]oxy}methyl)carbamate (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): 8.56 (br, 1H), 8.36 (br, 1H), 8.09 (br, 1H), 7.60 (s, 1H), 7.51 (d, 1H), 7.42 to 7.25 (m, 5H), 7.10 (d, 1H), 5.17 to 5.03 (dd, 2H), 4.73 (s, 2H), 4.61 (m, 1H), 4.37 (m, 1H), 3.95 (m, 1H), 2.79 (t, 2H), 2.48 (s, 2H), 1.72 to 1.56 (m, 5H), 0.90 (s, 6H); MS (EI) for C35H37N7O3: 604 (MH+).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-8818b69c7a7b440ea2543770d60ff966
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

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