N-(5-bromo-2-chloro-3-pyridinyl)methanesulfonamide → N-(2-chloro-5-(4-[7-(methyloxy)quinazolin-4-yl]-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)pyridin-3-yl)methanesulfonamide

HRID 241145Notes

Reaction equation

HRID 241145 reaction equation
Br[C:2]1[CH:3]=[C:4]([NH:9][S:10]([CH3:13])(=[O:12])=[O:11])[C:5]([Cl:8])=[N:6][CH:7]=1.[CH3:14][O:15][C:16]1[CH:25]=[C:24]2[C:19]([C:20]([N:26]3[CH2:32][C:31]4[CH:33]=[C:34](B(O)O)[CH:35]=[CH:36][C:30]=4[O:29][CH2:28][CH2:27]3)=[N:21][CH:22]=[N:23]2)=[CH:18][CH:17]=1>>[Cl:8][C:5]1[C:4]([NH:9][S:10]([CH3:13])(=[O:12])=[O:11])=[CH:3][C:2]([C:34]2[CH:35]=[CH:36][C:30]3[O:29][CH2:28][CH2:27][N:26]([C:20]4[C:19]5[C:24](=[CH:25][C:16]([O:15][CH3:14])=[CH:17][CH:18]=5)[N:23]=[CH:22][N:21]=4)[CH2:32][C:31]=3[CH:33]=2)=[CH:7][N:6]=1

Participants

3

Reactant 2

HCID 59519513N-(5-bromo-2-chloro-3-pyridinyl)methanesulfonamideHCID 66820289{4-[7-(Methyloxy)quinazolin-4-yl]-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl}boronic acid

Product 1

HCID 59586176N-(2-chloro-5-(4-[7-(methyloxy)quinazolin-4-yl]-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)pyridin-3-yl)methanesulfonamide

Procedure

Synthesized according to the method of example 5 using N-(5-bromo-2-chloropyridin-3-yl)methanesulfonamide (reagent preparation 25) and {4-[7-(methyloxy)quinazolin-4-yl]-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl}boronic acid (reagent preparation 23) in step 1. 1H NMR (400 MHz, d6-DMSO): 8.92 (br s, 1H), 8.75 (s, 1H), 8.62 (d, 1H), 8.19 (d, 1H), 8.10 (d, 1H), 7.89 (s, 1H), 7.62 (dd, 1H), 7.33 (dd, 1H), 7.25 (d, 1H), 7.04 (d, 1H), 5.41 (s, 2H), 4.65 (s, 2H), 4.47 (s, 2H), 3.96 (s, 3H), 3.19 (s, 3H); MS (EI) for C24H22ClN5O4S: 514 (MH+).

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-0dcfa8e9339c446caf445ab15be39100
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

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