4-Chloro-7-methoxy-2-methylquinazoline → HCID 178432069, compound

HRID 241162Notes

Reaction equation

HRID 241162 reaction equation
Cl[C:2]1[C:7]([CH:8]([CH3:10])[CH3:9])=[C:6]([CH3:11])[N:5]=[C:4]([CH2:12][N:13]([CH3:15])[CH3:14])[N:3]=1.[CH3:16][C:17]1[NH:49][C:20]2=[N:21][CH:22]=[C:23]([C:25]3[CH:26]=[CH:27][C:28]4[O:34][CH2:33][CH2:32][N:31](C5C6C(=CC(OC)=CC=6)N=C(C)N=5)[CH2:30][C:29]=4[CH:48]=3)[CH:24]=[C:19]2[N:18]=1.ClC1C2C(=CC(OC)=CC=2)N=C(C)N=1>>[CH3:14][N:13]([CH3:15])[CH2:12][C:4]1[N:5]=[C:6]([CH3:11])[C:7]([CH:8]([CH3:10])[CH3:9])=[C:2]([N:31]2[CH2:30][C:29]3[CH:48]=[C:25]([C:23]4[CH:24]=[C:19]5[N:18]=[C:17]([CH3:16])[NH:49][C:20]5=[N:21][CH:22]=4)[CH:26]=[CH:27][C:28]=3[O:34][CH2:33][CH2:32]2)[N:3]=1

Participants

4

Reactant 3

HCID 722070634-Chloro-7-methoxy-2-methylquinazolineHCID 790770781-(4-chloro-5-isopropyl-6-methylpyrimidin-2-yl)-N,N-dimethylmethanamineHCID 178487619HCID 178487619, compound

Product 1

HCID 178432069HCID 178432069, compound

Procedure

Synthesized according to the method of example 6 using 1-(4-chloro-5-isopropyl-6-methylpyrimidin-2-yl)-N,N-dimethylmethanamine (reagent preparation 17) in step 3. 1H NMR (400 MHZ, CDCl3): 12.78 (br, 1H), 8.51 (s, 1H), 8.08 (br, 1H), 7.46 (d, 1H), 7.43 (s, 1H), 7.14 (d, 1H), 4.37 (s, 2H), 4.30 (tr, 2H), 3.76 (tr, 2H), 3.55 (s, 2H), 3.40 (m, 1H), 2.75 (s, 3H), 2.55 (s, 3H), 2.34 (s, 6H), 1.35 (d, 6H). MS (EI) for C28H34N7O: 472 (MH+). 7-(2-methyl-3H-imidazo[4,5-b]pyridin-6-yl)-4-[2-methyl-7-(methyloxy)quinazolin-4-yl]-2,3,4,5-tetrahydro-1,4-benzoxazepine. Synthesized according to the method of example 6 using 4-chloro-7-methoxy-2-methylquinazoline in step 3. 1H NMR (400 MHz, DMSO-d6) δ 8.53 (s, 1H), 8.06 (s, 1H), 7.90 (d, 1H), 7.74 (d, 1H), 7.56 (dd, 1H), 7.11 (d, 1H), 7.03 (m, 3H), 5.02 (s, 3H), 4.41 (t, 3H), 4.11 (d, J=36.2 Hz, 3H), 3.88 (s, 5H), 2.55 (s, 5H), 2.43 (s, 5H), 1.90 (s, 1H); MS (EI) for C26H24N6O2: 453.3 (MH+).

Workup

  1. customSynthesized
  2. customSynthesized

Sources & evidence

ORD record
ord-2bbba230e9e24fa395b7078fd108ea2d
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

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