Triethylamine → ethyl 4-[(N-(methoxycarbonylmethyl)glycyl)amino]-N-(3,4-dichlorobenzyl)indole-2-carboxylate

HRID 1072567Notes

Reaction equation

Cl[CH2:2][C:3]([NH:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[CH:8]=[C:9]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[N:10]2[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=1)=[O:4].Cl.[CH3:30][O:31][C:32](=[O:35])[CH2:33][NH2:34].C(N(CC)CC)C>COC(O)C>[CH3:30][O:31][C:32]([CH2:33][NH:34][CH2:2][C:3]([NH:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[CH:8]=[C:9]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[N:10]2[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=1)=[O:4])=[O:35]

Participants

Conditions

Temperature: 100 °C

Procedure

Ethyl 4-chloroacetamido-N-(3,4-dichlorobenzyl)indole-2-carboxylate (0.4 g), glycine methyl ester hydrochloride (0.57 g) and triethylamine (1.25 ml) were dissolved in methoxyethanol (4.0 ml) and the reaction heated at 100° C. for 6 hours. The reaction was cooled and partitioned between water and ethyl acetate. Combined organic extracts were dried (MgSO4) and concentrated and the residue purified by chromatography using toluene:ethyl acetate (1:1) as eluent to give the product, ethyl 4-[(N-(methoxycarbonylmethyl)glycyl)amino]-N-(3,4-dichlorobenzyl)indole-2-carboxylate, as a pale yellow solid (0.17 g, 38%); NMR d (CD3SOCD3) 1.28 (t, 3H), 3.44 (s, 2H), 3.50 (s, 2H), 3.63 (s, 3H), 4.28 (q, 2H), 5.82 (s, 2H), 6.88 (dd, 1H), 7.10-7.30 (m, 4H), 7.50 (d, 1H), 7.69 (s, 1H), 7.80 (dd, 1H), 10.00 (brs, 1H); M/z (+) 494, 492 (M+).

Workup

temperatureThe reaction was cooled
custompartitioned between water and ethyl acetate
dry with materialCombined organic extracts were dried (MgSO4)
concentrationconcentrated
customthe residue purified by chromatography

Sources & evidence

ORD record: ord-32a9c4d335fe4975aa04f4a397029803
Source dataset: uspto-grants-2005_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06911465B1

Reaction notes

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