Triethylamine → methyl (7R)-7-[(2-{3-[(tert-butoxycarbonyl)(methyl)amino]pyrrolidin-1-yl}ethyl)(methyl)amino]-14-cyclohexyl-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate

HRID 1669456Notes

Reaction equation

[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:28]([O:30][CH3:31])=[O:29])=[CH:12][C:13]=3[N:14]3[C:21]=2[C:20]2[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=2[O:18][CH2:17][C@H:16]([NH:26][CH3:27])[CH2:15]3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:32]([O:36][C:37](=[O:48])[NH:38][CH2:39]C1CCN(CCCl)C1)([CH3:35])([CH3:34])[CH3:33].[CH3:49][CH2:50][N:51]([CH2:54][CH3:55])[CH2:52][CH3:53]>CC#N>[C:32]([O:36][C:37]([N:38]([CH3:39])[CH:49]1[CH2:53][CH2:52][N:51]([CH2:54][CH2:55][N:26]([CH3:27])[C@@H:16]2[CH2:15][N:14]3[C:13]4[CH:12]=[C:11]([C:28]([O:30][CH3:31])=[O:29])[CH:10]=[CH:9][C:8]=4[C:7]([CH:1]4[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]4)=[C:21]3[C:20]3[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=3[O:18][CH2:17]2)[CH2:50]1)=[O:48])([CH3:35])([CH3:34])[CH3:33]

Participants

Conditions

Temperature: 140 °C

Procedure

A solution of methyl (7R)-14-cyclohexyl-7-(methylamino)-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate (1 eq) in MeCN was treated with tert-butyl[1-(2-chloroethyl)pyrrolidin-3-yl]methylcarbamate (2.4 eq) and NEt3 (2 eq) and heated at 140° C. in a microwave oven. The solvent was removed in vacuo and the residue purified by FC (Biotage; DCM/MeOH) to get the title compound as a white powder (64%). (ES+) m/z 645 (M+H)+.

Workup

customThe solvent was removed in vacuo
customthe residue purified by FC (Biotage; DCM/MeOH)

Sources & evidence

ORD record: ord-62c4892ede2b462c8f373118502f95a6
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07989438B2

Reaction notes

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