[4-(6,6-Dimethyl-5,6,7,8-tetrahydroquinazolin-4-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl]boronic acid → 4-({2-Amino-5-[4-(6,6-dimethyl-5,6,7,8-tetrahydroquinazolin-4-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl]pyridin-3-yl}sulfonyl)-2-methylbutan-2-ol

HRID 241130Notes

Reaction equation

HRID 241130 reaction equation
[NH2:1][C:2]1[C:7]([S:8]([CH2:11][CH2:12][C:13]([CH3:16])([OH:15])[CH3:14])(=[O:10])=[O:9])=[CH:6][C:5](Br)=[CH:4][N:3]=1.[CH3:18][C:19]1([CH3:43])[CH2:28][CH2:27][C:26]2[N:25]=[CH:24][N:23]=[C:22]([N:29]3[CH2:35][C:34]4[CH:36]=[C:37](B(O)O)[CH:38]=[CH:39][C:33]=4[O:32][CH2:31][CH2:30]3)[C:21]=2[CH2:20]1>>[NH2:1][C:2]1[C:7]([S:8]([CH2:11][CH2:12][C:13]([CH3:16])([OH:15])[CH3:14])(=[O:10])=[O:9])=[CH:6][C:5]([C:37]2[CH:38]=[CH:39][C:33]3[O:32][CH2:31][CH2:30][N:29]([C:22]4[C:21]5[CH2:20][C:19]([CH3:18])([CH3:43])[CH2:28][CH2:27][C:26]=5[N:25]=[CH:24][N:23]=4)[CH2:35][C:34]=3[CH:36]=2)=[CH:4][N:3]=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 668207114-[(2-Amino-5-bromopyridin-3-yl)sulfonyl]-2-methylbutan-2-ol

Product 1

HCID 595863284-({2-Amino-5-[4-(6,6-dimethyl-5,6,7,8-tetrahydroquinazolin-4-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl]pyridin-3-yl}sulfonyl)-2-methylbutan-2-ol

Procedure

Prepared according to the method of example 5 by using 4-[(2-amino-5-bromopyridin-3-yl)sulfonyl]-2-methylbutan-2-ol (reagent preparation 41) 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): 8.52 (s, 1H), 8.35 (s, 1H), 8.14 (s, 1H), 7.50 (s, 1H), 7.43 (d, 1H), 7.06 (d, 1H), 4.70 (s, 2H), 4.30 (m, 2H), 3.95 (m, 2H), 3.35 (m, 2H), 2.79 (t, 2H), 2.48 (s, 2H), 1.82 (m, 2H), 1.68 (t, 2H), 1.15 (s, 6H), 0.90 (s, 6H); MS (EI) for C29H37N5O4S: 552 (MH+).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-0e18a0aa983e44949dae55f1d6d122ce
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

Loading…