[4-(6,6-Dimethyl-5,6,7,8-tetrahydroquinazolin-4-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl]boronic acid → 2-amino-5-[4-(6,6-dimethyl-5,6,7,8-tetrahydroquinazolin-4-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl]-N-{[(3S)-1-methylpyrrolidin-3-yl]methyl}pyridine-3-sulfonamide

HRID 241128Notes

Reaction equation

HRID 241128 reaction equation
[NH2:1][C:2]1[C:7]([S:8]([NH:11][CH2:12][C@H:13]2[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14]2)(=[O:10])=[O:9])=[CH:6][C:5](Br)=[CH:4][N:3]=1.[CH3:20][C:21]1([CH3:45])[CH2:30][CH2:29][C:28]2[N:27]=[CH:26][N:25]=[C:24]([N:31]3[CH2:37][C:36]4[CH:38]=[C:39](B(O)O)[CH:40]=[CH:41][C:35]=4[O:34][CH2:33][CH2:32]3)[C:23]=2[CH2:22]1>>[NH2:1][C:2]1[C:7]([S:8]([NH:11][CH2:12][C@H:13]2[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14]2)(=[O:10])=[O:9])=[CH:6][C:5]([C:39]2[CH:40]=[CH:41][C:35]3[O:34][CH2:33][CH2:32][N:31]([C:24]4[C:23]5[CH2:22][C:21]([CH3:20])([CH3:45])[CH2:30][CH2:29][C:28]=5[N:27]=[CH:26][N:25]=4)[CH2:37][C:36]=3[CH:38]=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 687785762-amino-5-bromo-N-{[(3S)-1-methylpyrrolidin-3-yl]methyl}pyridine-3-sulfonamide

Product 1

HCID 595865832-amino-5-[4-(6,6-dimethyl-5,6,7,8-tetrahydroquinazolin-4-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl]-N-{[(3S)-1-methylpyrrolidin-3-yl]methyl}pyridine-3-sulfonamide

Procedure

Prepared according to the method of example 5 by using 2-amino-5-bromo-N-{[(3S)-1-methylpyrrolidin-3-yl]methyl}pyridine-3-sulfonamide (reagent preparation 25) 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): 8.44 (br, 1H), 8.34 (s, 1H), 8.17 (s, 1H), 7.50 (s, 1H), 7.40 (d, 1H), 7.05 (d, 1H), 4.70 (s, 2H), 4.31 (m, 2H), 3.97 (m, 2H), 3.16 (m, 1H), 3.04 (t, 2H), 2.94 (d, 2H), 2.67 (t, 2H), 2.67 (s, 3H), 2.47 (s, 2H), 2.52 (m, 1H), 2.10 (m, 1H), 1.90 (m, 1H), 1.65 (m, 3H), 0.92 (s, 6H); MS (EI) for C29H37N7O3S: 564 (MH+).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-3dd16b26e6bd491ba5409c57016f28de
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

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