[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}sulfinyl)-2-methylbutan-2-ol

HRID 241131Notes

Reaction equation

HRID 241131 reaction equation
[NH2:1][C:2]1[C:7]([S:8]([CH2:10][CH2:11][C:12]([CH3:15])([OH:14])[CH3:13])=[O:9])=[CH:6][C:5](Br)=[CH:4][N:3]=1.[CH3:17][C:18]1([CH3:42])[CH2:27][CH2:26][C:25]2[N:24]=[CH:23][N:22]=[C:21]([N:28]3[CH2:34][C:33]4[CH:35]=[C:36](B(O)O)[CH:37]=[CH:38][C:32]=4[O:31][CH2:30][CH2:29]3)[C:20]=2[CH2:19]1>>[NH2:1][C:2]1[C:7]([S:8]([CH2:10][CH2:11][C:12]([CH3:15])([OH:14])[CH3:13])=[O:9])=[CH:6][C:5]([C:36]2[CH:37]=[CH:38][C:32]3[O:31][CH2:30][CH2:29][N:28]([C:21]4[C:20]5[CH2:19][C:18]([CH3:17])([CH3:42])[CH2:27][CH2:26][C:25]=5[N:24]=[CH:23][N:22]=4)[CH2:34][C:33]=3[CH:35]=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 668205914-[(2-Amino-5-bromopyridin-3-yl)sulfinyl]-2-methylbutan-2-ol

Product 1

HCID 595864404-({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}sulfinyl)-2-methylbutan-2-ol

Procedure

Prepared according to the method of example 5 by using 4-[(2-amino-5-bromopyridin-3-yl)sulfinyl]-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): 8.40 (s, 1H), 8.34 (s, 1H), 8.03 (s, 1H), 7.51 (s, 1H), 7.42 (d, 1H), 7.05 (d, 1H), 4.68 (s, 2H), 4.33 (m, 2H), 3.94 (m, 2H), 3.20 (m, 2H), 2.79 (t, 2H), 2.47 (s, 2H), 1.80 (m, 2H), 1.67 (t, 2H), 1.21 (s, 6H), 0.88 (s, 6H); MS (EI) for C29H37N5O3S: 536 (MH+).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-2325ebf5c8be4679837320c700239be2
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

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