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

HRID 241123Notes

Reaction equation

HRID 241123 reaction equation
C1(COC(=O)[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)C=CC=CC=1.[CH2:40]([C@@H:42]1[CH2:51][C:50]2[N:49]=[CH:48][N:47]=[C:46]([N:52]3[CH2:58][C:57]4[CH:59]=[C:60](B(O)O)[CH:61]=[CH:62][C:56]=4[O:55][CH2:54][CH2:53]3)[C:45]=2[CH2:44][CH2:43]1)[CH3:41]>>[CH2:40]([C@@H:42]1[CH2:51][C:50]2[N:49]=[CH:48][N:47]=[C:46]([N:52]3[CH2:58][C:57]4[CH:59]=[C:60]([C:27]5[CH:28]=[C:23]6[NH:22][C:21]([C@H:19]([NH2:10])[CH3:20])=[N:30][C:24]6=[N:25][CH:26]=5)[CH:61]=[CH:62][C:56]=4[O:55][CH2:54][CH2:53]3)[C:45]=2[CH2:44][CH2:43]1)[CH3:41]

Participants

3

Reactant 2

HCID 66820686{4-[(7S)-7-ethyl-5,6,7,8-tetrahydroquinazolin-4-yl]-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl}boronic acidHCID 68773284Phenylmethyl{(1R)-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 57389823(1R)-1-(6-{4-[(7S)-7-ethyl-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)ethanamine

Procedure

Prepared according to the method of example 5 by using phenylmethyl{(1R)-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-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): 8.59 (s, 1H), 8.31 (s, 1H), 8.12 (s, 1H), 7.61 (s, 1H), 7.50 (d, 1H), 7.09 (d, 1H), 4.80 (m, 2H), 4.53 (m, 1H), 4.43 (m, 1H), 4.27 (m, 1H), 4.06 to 3.93 (m, 2H), 2.96 to 2.78 (m, 2H), 2.62 (m, 1H), 2.32 (m, 1H), 1.95 (m, 1H), 1.75 (m, 1H), 1.67 (d, 3H), 1.41 (m, 2H), 1.16 (m, 1H), 0.99 (t, 3H); MS (EI) for C27H31N7O: 470 (MH+).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-8472f325b6bb40cd8cb5c8580ecec9cd
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

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