1,1-dimethylethyl 7-(6-amino-5-nitropyridin-3-yl)-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate → N-ethyl-6-{4-[2-methyl-7-(methyloxy)quinazolin-4-yl]-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl}-1H-imidazo[4,5-b]pyridin-2-amine

HRID 241183Notes

Reaction equation

HRID 241183 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]3[O:17][CH2:16][CH2:15][N:14]([C:18](OC(C)(C)C)=O)[CH2:13][C:12]=3[CH:25]=2)=[CH:4][C:3]=1[N+:26]([O-])=O.ClC1[C:39]2[C:34](=[CH:35][C:36]([O:40][CH3:41])=[CH:37][CH:38]=2)[N:33]=[C:32]([CH3:42])[N:31]=1>>[CH2:6]([NH:7][C:2]1[NH:26][C:3]2[C:2]([N:1]=1)=[N:7][CH:6]=[C:5]([C:8]1[CH:9]=[CH:10][C:11]3[O:17][CH2:16][CH2:15][N:14]([C:18]4[C:39]5[C:34](=[CH:35][C:36]([O:40][CH3:41])=[CH:37][CH:38]=5)[N:33]=[C:32]([CH3:42])[N:31]=4)[CH2:13][C:12]=3[CH:25]=1)[CH:4]=2)[CH3:5]

Participants

3

Reactant 2

HCID 668202001,1-dimethylethyl 7-(6-amino-5-nitropyridin-3-yl)-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylateHCID 722070634-Chloro-7-methoxy-2-methylquinazoline

Product 1

HCID 49805310N-ethyl-6-{4-[2-methyl-7-(methyloxy)quinazolin-4-yl]-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl}-1H-imidazo[4,5-b]pyridin-2-amine

Procedure

Prepared according to the method of example 11 by using tert-butyl 7-(6-amino-5-nitropyridin-3-yl)-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate (Example 26) in step 1 and 4-chloro-7-methoxy-2-methylquinazoline in step 4. 1H NMR (400 MHz, DMSO-d6) δ 8.22 (s, 0.5H), 8.07 (s, 0.5H), 7.90 (d, 1H), 7.68-7.42 (m, 3H), 7.17-6.84 (m, 4H), 5.00 (s, 2H), 4.47-4.39 (m, 2H), 4.18-4.10 (m, 2H), 3.88 (s, 3H), 3.40-3.30 (m, 2H), 2.43 (s, 3H), 1.26-1.13 (m, 3H); MS (EI) for C27H27N7O2: 482 (MH+).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-f34d87a289ab47308f2061ad6775398a
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

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