Morpholine → methyl 2-(2-acetylphenyl)-3-cyclohexyl-1H-indole-6-carboxylate

HRID 1453363Notes

Reaction equation

[CH:1]1[C:11]2[C:10]3=[CH:12][C:13]4[CH:14]=[CH:15][C:16]([C:19]([OH:21])=[O:20])=[CH:17][C:18]=4[N:9]3CC=C[C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH:22]1[C:32]2C3=CC4C=CC(C(O)=O)=CC=4N3C=CC[C:26]=2[CH:25]=[CH:24][CH:23]=1.C1C2C3=CC4C=C[C:58]([C:61](O)=[O:62])=CC=4N3CC(C(O)=O)=CC=2C=CC=1.[CH3:67]N(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C.N1CCOCC1>CS(C)=O>[C:61]([C:5]1[CH:4]=[CH:3][CH:2]=[CH:1][C:11]=1[C:10]1[NH:9][C:18]2[C:13]([C:12]=1[CH:22]1[CH2:32][CH2:26][CH2:25][CH2:24][CH2:23]1)=[CH:14][CH:15]=[C:16]([C:19]([O:21][CH3:67])=[O:20])[CH:17]=2)(=[O:62])[CH3:58]

Participants

Procedure

7H-indolo[2,1-a][2]benzazepine-10-carboxylic acid, 13-cyclohexyl-5-methyl-6-(4-morpholinylcarbonyl)-, methyl ester. To a solution of 7H-indolo[2,1-a][2]benzazepine-6,10-dicarboxylic acid, 13-cyclohexyl-5-methyl-, 10-methyl ester (120 mg, 0.28 mmol) in DMSO (3.0 mL), TBTU (135 mg, 0.42 mmol) and DIPEA (0.244 mL, 1.4 mmol) were added. The reaction mixture was stirred at rt for 15 min. Then morpholine (0.037 mL, 0. 42 mmol) was added and the reaction mixture was stirred at rt for overnight. It was then concentrated under reduced pressure and the residue was purified by Prep. reverse phase HPLC to give the title compound as a white solid, (115 mg, 82% yield). MS m/z 499(MH+); 1H NMR (500 MHz, CD3OD) δ ppm Compound exists as a complex mixture of rotamers.

Workup

stirringthe reaction mixture was stirred at rt for overnight
concentrationIt was then concentrated under reduced pressure
customthe residue was purified by Prep

Sources & evidence

ORD record: ord-8a9357df51444150a0e12e23db425a44
Source dataset: uspto-grants-2009_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07473688B2

Reaction notes

Loading…

Reaction equation

Participants

Reactant 6

Product 1

Reagents, catalysts & solvents 1

Procedure

Workup

Sources & evidence

Reaction notes