2-amino-5-bromo-N-((1-methylpiperidin-4-yl)methyl)pyridine-3-sulfonamide → 2-amino-N-[(1-methylpiperidin-4-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 241114Notes

Reaction equation

HRID 241114 reaction equation
[CH3:1][C:2]1([CH3:27])[C:11]([CH3:12])=[CH:10][C:9]2[N:8]=[CH:7][N:6]=[C:5]([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:4]=2[CH2:3]1.[NH2:28][C:29]1[C:34]([S:35]([NH:38][CH2:39][CH:40]2[CH2:45][CH2:44][N:43]([CH3:46])[CH2:42][CH2:41]2)(=[O:37])=[O:36])=[CH:33][C:32](Br)=[CH:31][N:30]=1>>[NH2:28][C:29]1[C:34]([S:35]([NH:38][CH2:39][CH:40]2[CH2:41][CH2:42][N:43]([CH3:46])[CH2:44][CH2:45]2)(=[O:37])=[O:36])=[CH:33][C:32]([C:21]2[CH:22]=[CH:23][C:17]3[O:16][CH2:15][CH2:14][N:13]([C:5]4[C:4]5[CH2:3][C:2]([CH3:1])([CH3:27])[C:11]([CH3:12])=[CH:10][C:9]=5[N:8]=[CH:7][N:6]=4)[CH2:19][C:18]=3[CH:20]=2)=[CH:31][N:30]=1

Participants

3

Reactant 2

HCID 621527292-amino-5-bromo-N-((1-methylpiperidin-4-yl)methyl)pyridine-3-sulfonamideHCID 66820081[4-(6,6,7-Trimethyl-5,6-dihydroquinazolin-4-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl]boronic acid

Product 1

HCID 668205462-amino-N-[(1-methylpiperidin-4-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 example 5 by using [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) and 2-amino-5-bromo-N-((1-methylpiperidin-4-yl)methyl)pyridine-3-sulfonamide (reagent preparation 25) in step 1. 1H NMR (400 MHz, DMSO-d6) δ 8.50 (d, 1H), 8.37 (s, 1H), 8.03 (d, 1H), 7.84 (t, 1H), 7.55 (d, 1H), 7.45 (dd, 1H), 7.02 (d, 1H), 6.67 (br s, 2H), 6.13 (d, 1H), 4.62 (s, 2H), 4.37-4.29 (m, 2H), 3.88-3.78 (m, 2H), 2.72-2.60 (m, 6H), 2.07 (s, 3H), 1.88 (s, 3H), 1.74-1.62 (m, 2H), 1.61-1.50 (m, 2H), 1.34-1.16 (m, 1H), 1.09-0.95 (m, 2H), 0.91 (s, 6H); MS (EI) for C32H41N7O3S: 604 (MH+).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-f11f804736104262a4ff422ca7272847
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

Loading…