{4-[7-(Methyloxy)quinazolin-4-yl]-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl}boronic acid → HCID 59586469, compound

HRID 241146Notes

Reaction equation

HRID 241146 reaction equation
Br[C:2]1[CH:3]=[C:4]2[N:10]=[C:9]([NH:11][C:12](=[O:14])[CH3:13])[S:8][C:5]2=[N:6][CH:7]=1.[CH3:15][O:16][C:17]1[CH:26]=[C:25]2[C:20]([C:21]([N:27]3[CH2:33][C:32]4[CH:34]=[C:35](B(O)O)[CH:36]=[CH:37][C:31]=4[O:30][CH2:29][CH2:28]3)=[N:22][CH:23]=[N:24]2)=[CH:19][CH:18]=1>>[CH3:21][N:27]([CH2:33][C:23]1[N:22]=[C:21]([N:27]2[CH2:33][C:32]3[CH:34]=[C:35]([C:2]4[CH:3]=[C:4]5[N:10]=[C:9]([NH:11][C:12](=[O:14])[CH3:13])[S:8][C:5]5=[N:6][CH:7]=4)[CH:36]=[CH:37][C:31]=3[O:30][CH2:29][CH2:28]2)[C:20]2[C:25](=[CH:26][C:17]([O:16][CH3:15])=[CH:18][CH:19]=2)[N:24]=1)[CH3:28]

Participants

3

Reactant 2

HCID 66820289{4-[7-(Methyloxy)quinazolin-4-yl]-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl}boronic acidHCID 73553785HCID 73553785, compound

Product 1

HCID 59586469HCID 59586469, compound

Procedure

Synthesized according to the method of example 5 using N-(6-bromothiazolo[5,4-b]pyridin-2-yl)acetamide (J. Heterocyclic Chemistry 2003, 40, 261) 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) δ 12.60 (s, 1H), 8.86 (d, 1H), 8.45 (d, 1H), 8.23-8.07 (m, 2H), 7.70 (dd, 1H), 7.27-7.17 (m, 2H), 7.02 (d, 1H), 5.43 (s, 2H), 4.65-4.57 (m, 2H), 4.46 (s, 2H), 4.43-4.37 (m, 2H), 3.94 (s, 3H), 2.73 (s, 6H), 2.25 (s, 3H); MS (EI) for C29H29N7O3S: 556 (MH+).

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-fdd7935f26644aedb50f072bc44e402f
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

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