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

HRID 241129Notes

Reaction equation

HRID 241129 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([CH3:46])[C:30]([CH3:31])=[CH:29][C:28]2[N:27]=[CH:26][N:25]=[C:24]([N:32]3[CH2:38][C:37]4[CH:39]=[C:40](B(O)O)[CH:41]=[CH:42][C:36]=4[O:35][CH2:34][CH2:33]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:40]2[CH:41]=[CH:42][C:36]3[O:35][CH2:34][CH2:33][N:32]([C:24]4[C:23]5[CH2:22][C:21]([CH3:20])([CH3:46])[C:30]([CH3:31])=[CH:29][C:28]=5[N:27]=[CH:26][N:25]=4)[CH2:38][C:37]=3[CH:39]=2)=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 66820081[4-(6,6,7-Trimethyl-5,6-dihydroquinazolin-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 595863182-amino-N-{[(3S)-1-methylpyrrolidin-3-yl]methyl}-5-[4-(6,6,7-trimethyl-5,6-dihydroquinazolin-4-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl]pyridine-3-sulfonamide

Procedure

Prepared according to the method of 5 by using 2-amino-5-bromo-N-{[(3S)-1-methylpyrrolidin-3-yl]methyl}pyridine-3-sulfonamide (reagent preparation 25) and [4-(6,6,7-trimethyl-5,6-dihydroquinazolin-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): 8.35 (s, 1H), 8.25 (s, 1H), 8.07 (s, 1H), 7.37 (s, 1H), 7.32 (d, 1H), 6.97 (d, 1H), 6.07 (s, 1H), 4.58 (s, 2H), 4.23 (m, 2H), 3.84 (m, 2H), 2.86 to 2.78 (m, 3H), 2.72 (m, 2H), 2.63 (s, 2H), 2.46 (m, 1H), 2.40 (s, 3H), 2.34 (m, 1H), 1.93 (m, 1H), 1.83 (s, 3H), 1.46 (m, 1H), 0.99 (s, 6H); MS (EI) for C31H39N7O3S: 590 (MH+).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-2c4a4d91ca3444dcb8d7effb33113771
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

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