1,1,1-Trimethoxypropane → 4-(6,6-dimethyl-5,6,7,8-tetrahydroquinazolin-4-yl)-7-(2-ethyl-1H-benzimidazol-6-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepine

HRID 241204Notes

Reaction equation

HRID 241204 reaction equation
[CH3:1][C:2]1([CH3:31])[CH2:11][CH2:10][C:9]2[N:8]=[CH:7][N:6]=[C:5]([N:12]3[CH2:18][C:17]4[CH:19]=[C:20]([C:23]5[CH:24]=[C:25]([NH2:30])[C:26]([NH2:29])=[CH:27][CH:28]=5)[CH:21]=[CH:22][C:16]=4[O:15][CH2:14][CH2:13]3)[C:4]=2[CH2:3]1.[C:32](OC)(OC)(OC)[CH2:33][CH3:34]>>[CH3:1][C:2]1([CH3:31])[CH2:11][CH2:10][C:9]2[N:8]=[CH:7][N:6]=[C:5]([N:12]3[CH2:18][C:17]4[CH:19]=[C:20]([C:23]5[CH:28]=[CH:27][C:26]6[N:29]=[C:32]([CH2:33][CH3:34])[NH:30][C:25]=6[CH:24]=5)[CH:21]=[CH:22][C:16]=4[O:15][CH2:14][CH2:13]3)[C:4]=2[CH2:3]1

Participants

3

Reactant 2

HCID 1411451,1,1-TrimethoxypropaneHCID 66820700HCID 66820700, compound

Product 1

HCID 595862774-(6,6-dimethyl-5,6,7,8-tetrahydroquinazolin-4-yl)-7-(2-ethyl-1H-benzimidazol-6-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepine

Procedure

Prepared according to the method of example 18 omitting step 1 and by using 4-[4-(6,6-dimethyl-5,6,7,8-tetrahydroquinazolin-4-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl]benzene-1,2-diamine and trimethyl orthopropionate in step 2. 1H NMR (400 MHz, d6-DMSO): 8.69 (s, 1H), 7.94 (s, 1H), 7.84-7.78 (m, 3H), 7.60 (m, 1H), 7.35 (s, 1H), 7.23 (s, 1H), 7.04 (d, 1H), 5.09 (s, 2H), 4.48 (m, 2H), 4.19 (m, 2H), 3.18 (dd, 2H), 2.70 (t, 2H), 2.54 (s, 2H), 1.58 (t, 2H), 1.45 (t, 3H), 0.85 (s, 6H); MS (EI) for C28H31N5O: 454 (MH+).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-6b93e745a649452188853cb555dd5368
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

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