Bromomethylcyclopropane → 4-{7-[(cyclopropylmethyl)oxy]-8-(methyloxy)quinazolin-4-yl}-7-(2-methyl-1H-benzimidazol-6-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepine

HRID 241175Notes

Reaction equation

HRID 241175 reaction equation
[CH3:1][C:2]1[NH:6][C:5]2[CH:7]=[C:8]([C:11]3[CH:12]=[CH:13][C:14]4[O:20][CH2:19][CH2:18][N:17]([C:21]5[C:30]6[C:25](=[C:26]([O:39][CH3:40])[C:27]([O:31]CC7C=CC=CC=7)=[CH:28][CH:29]=6)[N:24]=[CH:23][N:22]=5)[CH2:16][C:15]=4[CH:41]=3)[CH:9]=[CH:10][C:4]=2[N:3]=1.[CH:42]1([CH2:45]Br)[CH2:44][CH2:43]1>>[CH:42]1([CH2:45][O:31][C:27]2[C:26]([O:39][CH3:40])=[C:25]3[C:30]([C:21]([N:17]4[CH2:16][C:15]5[CH:41]=[C:11]([C:8]6[CH:9]=[CH:10][C:4]7[N:3]=[C:2]([CH3:1])[NH:6][C:5]=7[CH:7]=6)[CH:12]=[CH:13][C:14]=5[O:20][CH2:19][CH2:18]4)=[N:22][CH:23]=[N:24]3)=[CH:29][CH:28]=2)[CH2:44][CH2:43]1

Participants

3

Reactant 2

HCID 81503BromomethylcyclopropaneHCID 59586620HCID 59586620, compound

Product 1

HCID 573894274-{7-[(cyclopropylmethyl)oxy]-8-(methyloxy)quinazolin-4-yl}-7-(2-methyl-1H-benzimidazol-6-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepine

Procedure

Synthesized according to the method of example 10 using 7-(2-methyl-1H-benzimidazol-6-yl)-4-{8-(methyloxy)-7-[(phenylmethyl)oxy]quinazolin-4-yl}-2,3,4,5-tetrahydro-1,4-benzoxazepine (example 1) in step 1 and cyclopropylmethyl bromide in step 2. 1H NMR (400 MHz, d6-DMSO): 8.66 (s, 1H), 8.08 (s, 1H), 7.92 (s, 1H), 7.81 (m, 3H), 7.63 (d, 1H), 7.50 (d, 1H), 7.04 (d, 1H), 5.44 (s, 2H), 4.63 (br s, 3H) 4.53 (br s, 2H), 4.17 (d, 2H), 3.92 (s, 3H), 0.83 (m, 1H), 0.61 (m, 2H), 0.41 (m, 2H); MS (EI) for C30H29N5O3: 508 (MH+).

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-77a1f384d3fa4355932ab95e49fb92d2
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

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