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

HRID 241110Notes

Reaction equation

HRID 241110 reaction equation
[CH2:1]([C@@H:3]1[CH2:12][C:11]2[N:10]=[CH:9][N:8]=[C:7]([N:13]3[CH2:19][C:18]4[CH:20]=[C:21](B(O)O)[CH:22]=[CH:23][C:17]=4[O:16][CH2:15][CH2:14]3)[C:6]=2[CH2:5][CH2:4]1)[CH3:2].[NH2:27][C:28]1[C:33]([S:34]([N:37]2[CH2:41][CH2:40][C@@H:39]([NH:42]C(=O)OC(C)(C)C)[CH2:38]2)(=[O:36])=[O:35])=[CH:32][C:31](Br)=[CH:30][N:29]=1>>[NH2:42][C@@H:39]1[CH2:40][CH2:41][N:37]([S:34]([C:33]2[C:28]([NH2:27])=[N:29][CH:30]=[C:31]([C:21]3[CH:22]=[CH:23][C:17]4[O:16][CH2:15][CH2:14][N:13]([C:7]5[C:6]6[CH2:5][CH2:4][C@H:3]([CH2:1][CH3:2])[CH2:12][C:11]=6[N:10]=[CH:9][N:8]=5)[CH2:19][C:18]=4[CH:20]=3)[CH:32]=2)(=[O:35])=[O:36])[CH2:38]1

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 68774110(R)-tert-butyl 1-(2-amino-5-bromopyridin-3-ylsulfonyl)pyrrolidin-3-ylcarbamate

Product 1

HCID 595864873-{[(3R)-3-aminopyrrolidin-1-yl]sulfonyl}-5-{4-[(7S)-7-ethyl-5,6,7,8-tetrahydroquinazolin-4-yl]-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl}pyridin-2-amine

Procedure

Prepared according to the method of example 5 by using {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) and 1,1-dimethylethyl {(3R)-1-[(2-amino-5-bromopyridin-3-yl)sulfonyl]pyrrolidin-3-yl}carbamate (reagent preparation 25) in step 1. 1H NMR (400 MHz, d6-DMSO): 8.53 (d, 1H), 8.33 (s, 1H), 7.99 (d, 1H), 7.57 (d, 1H), 7.44 (dd, 1H), 7.01 (d, 1H), 6.75 (brs, 2H), 4.70 (dd, 2H), 4.36 (m, 1H), 4.24 (m, 1H), 3.86 (m, 2H), 3.36 (m, 2H), 3.26 (m, 2H), 2.87, 2.83 (m, dd, 3H), 2.27 (dd, 1H), 1.89 (m, 3H), 1.68 (m, 1H), 1.52 (m, 1H), 1.37 (m, 2H), 1.11 (m, 1H), 0.94 (t, 3H); MS (EI) for C28H35N7O3S: 550 (MH+).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-e723d8c78f974fe5be4d46d1f6705953
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

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