2-amino-N-(2-amino-2-methylpropyl)-5-bromopyridine-3-sulfonamide → 2-amino-N-(2-amino-2-methylpropyl)-5-{4-[(7S)-7-ethyl-5,6,7,8-tetrahydroquinazolin-4-yl]-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl}pyridine-3-sulfonamide

HRID 241111Notes

Reaction equation

HRID 241111 reaction equation
[CH2:1]([C@@H:3]1[CH2:12][C:11]2[N:10]=[CH:9][N:8]=[C:7]([N:13]3[CH2:19][C:18]4[CH:20]=[C:21](B(O)O)[CH:22]=[CH:23][C:17]=4[O:16][CH2:15][CH2:14]3)[C:6]=2[CH2:5][CH2:4]1)[CH3:2].[NH2:27][C:28]1[C:33]([S:34]([NH:37][CH2:38][C:39]([NH2:42])([CH3:41])[CH3:40])(=[O:36])=[O:35])=[CH:32][C:31](Br)=[CH:30][N:29]=1>>[NH2:27][C:28]1[C:33]([S:34]([NH:37][CH2:38][C:39]([NH2:42])([CH3:40])[CH3:41])(=[O:36])=[O:35])=[CH:32][C:31]([C:21]2[CH:22]=[CH:23][C:17]3[O:16][CH2:15][CH2:14][N:13]([C:7]4[C:6]5[CH2:5][CH2:4][C@H:3]([CH2:1][CH3:2])[CH2:12][C:11]=5[N:10]=[CH:9][N:8]=4)[CH2:19][C:18]=3[CH:20]=2)=[CH:30][N:29]=1

Participants

3

Reactant 2

HCID 668201752-amino-N-(2-amino-2-methylpropyl)-5-bromopyridine-3-sulfonamideHCID 66820686{4-[(7S)-7-ethyl-5,6,7,8-tetrahydroquinazolin-4-yl]-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl}boronic acid

Product 1

HCID 668203182-amino-N-(2-amino-2-methylpropyl)-5-{4-[(7S)-7-ethyl-5,6,7,8-tetrahydroquinazolin-4-yl]-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl}pyridine-3-sulfonamide

Procedure

Prepared according to the method of example 5 by using {4-[(7S)-7-ethyl-5,6,7,8-tetrahydroquinazolin-4-yl]-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl}boronic acid (reagent preparation 23) and 2-amino-N-(2-amino-2-methylpropyl)-5-bromopyridine-3-sulfonamide (reagent preparation 25) in step 1. 1H NMR (400 MHz, d6-DMSO): 8.48 (d, 1H), 8.33 (s, 1H), 8.01 (d, 1H), 7.54 (d, 1H), 7.42 (dd, 1H), 7.01 (d, 1H), 7.72 (brs, 2H), 4.69 (dd, 2H), 4.37 (m, 1H), 4.23 (m, 1H), 3.85 (m, 2H), 2.93 (m, 2H), 2.60 (s, 2H), 2.27 (dd, 1H), 1.87 (m, 1H), 1.70 (m, 1H), 1.35 (m, 2H), 1.10 (m, 1H), 0.93 (t, 3H), 0.92 (s, 6H); MS (EI) for C28H37N7O3S: 552 (MH+).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-25b7d497bd054420bcf2628c337a87cf
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

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