2-Amino-5-bromopyridine → 4-[2-methyl-7-(methyloxy)quinazolin-4-yl]-7-(1H-pyrrolo[2,3-b]pyridin-5-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepine

HRID 241097Notes

Reaction equation

HRID 241097 reaction equation
[CH3:1][C:2]1[N:11]=[C:10]([N:12]2[CH2:18][C:17]3[CH:19]=[C:20]([C:23]4[CH:24]=[CH:25][C:26]([NH2:29])=[N:27][CH:28]=4)[CH:21]=[CH:22][C:16]=3[O:15][CH2:14][CH2:13]2)[C:9]2[C:4](=[CH:5][C:6]([O:30][CH3:31])=[CH:7][CH:8]=2)[N:3]=1.Br[C:33]1C=CC(N)=N[CH:38]=1.ClC1C2C(=CC(OC)=CC=2)N=C(C)N=1>>[CH3:1][C:2]1[N:11]=[C:10]([N:12]2[CH2:18][C:17]3[CH:19]=[C:20]([C:23]4[CH:24]=[C:25]5[CH:38]=[CH:33][NH:29][C:26]5=[N:27][CH:28]=4)[CH:21]=[CH:22][C:16]=3[O:15][CH2:14][CH2:13]2)[C:9]2[C:4](=[CH:5][C:6]([O:30][CH3:31])=[CH:7][CH:8]=2)[N:3]=1

Participants

4

Reactant 3

HCID 706222-Amino-5-bromopyridineHCID 595862345-{4-[2-Methyl-7-(methyloxy)quinazolin-4-yl]-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl}pyridin-2-amineHCID 722070634-Chloro-7-methoxy-2-methylquinazoline

Product 1

HCID 668214084-[2-methyl-7-(methyloxy)quinazolin-4-yl]-7-(1H-pyrrolo[2,3-b]pyridin-5-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepine

Procedure

(5-{4-[2-methyl-7-(methyloxy)quinazolin-4-yl]-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl}pyridin-2-amine. Synthesized according to the method of example 3 using 5-bromo-2-aminopyridine in step 1 and 4-chloro-7-methoxy-2-methylquinazoline in step 3. 1H NMR (400 MHz, DMSO-d6): 11.9 (s, 1H, AcOH), 8.21 (d, 1H), 7.87 (d, 1H), 7.67 (dd, 1H), 7.55 (m, 1H), 7.38 (dd, 1H), 7.10 (d, 1H), 7.02 (dd, 1H), 6.96 (d, 1H), 6.52 (d, 1H), 6.03 (s, 2H), 4.96 (s, 2H), 4.38 (m, 2H), 4.13 (m, 2H), 3.87 (s, 3H), 2.42 (s, 3H), 1.90 (s, 3H, AcOH); MS (EI) for C24H23N5O2: 413.9 (MH+).

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-e1665a03ccbc4f989797d5ac44d48455
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

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