[4-(6,6-Dimethyl-5,6-dihydroquinazolin-4-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl]boronic acid → 3-{[(3R)-3-aminopyrrolidin-1-yl]sulfonyl}-5-[4-(6,6-dimethyl-5,6-dihydroquinazolin-4-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl]pyridin-2-amine

HRID 241109Notes

Reaction equation

HRID 241109 reaction equation
[CH3:1][C:2]1([CH3:26])[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][N:6]=[C:5]([N:12]3[CH2:18][C:17]4[CH:19]=[C:20](B(O)O)[CH:21]=[CH:22][C:16]=4[O:15][CH2:14][CH2:13]3)[C:4]=2[CH2:3]1.[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:20]3[CH:21]=[CH:22][C:16]4[O:15][CH2:14][CH2:13][N:12]([C:5]5[C:4]6[CH2:3][C:2]([CH3:1])([CH3:26])[CH:11]=[CH:10][C:9]=6[N:8]=[CH:7][N:6]=5)[CH2:18][C:17]=4[CH:19]=3)[CH:32]=2)(=[O:35])=[O:36])[CH2:38]1

Participants

3

Reactant 2

HCID 66820559[4-(6,6-Dimethyl-5,6-dihydroquinazolin-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 595863753-{[(3R)-3-aminopyrrolidin-1-yl]sulfonyl}-5-[4-(6,6-dimethyl-5,6-dihydroquinazolin-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-(6,6-dimethyl-5,6-dihydroquinazolin-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): 8.57 (d, 1H), 8.41 (s, 1H), 8.02 (d, 1H), 7.58 (d, 1H), 7.47 (dd, 1H), 7.02 (d, 1H), 6.75 (brs, 2H), 6.26 (dd, 2H), 4.63 (s, 2H), 4.33 (m, 2H), 3.84 (m, 2H), 3.37 (m, 2H), 3.27 (m, 2H), 2.89 (m, 1H), 2.71 (s, 2H), 1.86 (m, 3H), 1.53 (m, 1H), 0.95 (s, 6H); MS (EI) for C28H33N7O3S: 548 (MH+).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-e5618d0ebb8a4e5d8a3a000d12ce0cd5
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

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