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 → phenylmethyl[(1S)-1-(6-{4-[(7s)-7-ethyl-2-methyl-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 241120Notes

Reaction equation

HRID 241120 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.[CH2:40]([C@@H:42]1[CH2:51][C:50]2[N:49]=[C:48]([CH3:52])[N:47]=[C:46]([N:53]3[CH2:59][C:58]4[CH:60]=[C:61](B(O)O)[CH:62]=[CH:63][C:57]=4[O:56][CH2:55][CH2:54]3)[C:45]=2[CH2:44][CH2:43]1)[CH3:41]>>[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:61]2[CH:62]=[CH:63][C:57]4[O:56][CH2:55][CH2:54][N:53]([C:46]5[C:45]6[CH2:44][CH2:43][C@H:42]([CH2:40][CH3:41])[CH2:51][C:50]=6[N:49]=[C:48]([CH3:52])[N:47]=5)[CH2:59][C:58]=4[CH:60]=2)[CH:28]=3)[CH3:20])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 2

HCID 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)carbamateHCID 68777066{4-[(7S)-7-ethyl-2-methyl-5,6,7,8-tetrahydroquinazolin-4-yl]-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl}boronic acid

Product 1

HCID 59586181phenylmethyl[(1S)-1-(6-{4-[(7s)-7-ethyl-2-methyl-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-[(7S)-7-ethyl-2-methyl-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): 8.54 (br, 1H), 8.05 (br, 1H), 7.61 (s, 1H), 7.48 (d, 1H), 7.41 to 7.29 (m, 5H), 7.09 (d, 1H), 4.77 (d, 2H), 4.61 (d, 2H), 4.43 (m, 1H), 4.20 (m, 1H), 4.04 (m, 1H), 3.95 (m, 1H), 3.88 (s, 3H), 3.29 (m, 1H), 2.87 (m, 1H), 2.78 (m, 1H), 2.60 (m, 1H), 2.35 (s, 3H), 2.29 (m, 1H), 1.96 (m, 1H), 1.69 (m, 1H), 1.63 (d, 3H), 1.41 (m, 2H), 1.16 (m, 1H), 0.99 (t, 3H); MS (EI) for C36H39N7O3: 618 (MH+).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-8bedbbe10e5a447eb5cc6ae4fdcd4eb9
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

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