Triethylamine → Phenyl N-(4-(1-(ethylamino)carbonyl-1H-5-indolyl)oxy-2-pyridyl)carbamate

HRID 2376860Notes

Reaction equation

C(N(CC)CC)C.[CH2:8]([NH:10][C:11]([N:13]1[C:21]2[C:16](=[CH:17][C:18]([O:22][C:23]3[CH:28]=[CH:27][N:26]=[C:25]([NH2:29])[CH:24]=3)=[CH:19][CH:20]=2)[CH:15]=[CH:14]1)=[O:12])[CH3:9].Cl[C:31]([O:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:32]>O1CCCC1>[CH2:8]([NH:10][C:11]([N:13]1[C:21]2[C:16](=[CH:17][C:18]([O:22][C:23]3[CH:28]=[CH:27][N:26]=[C:25]([NH:29][C:31](=[O:32])[O:33][C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[CH:24]=3)=[CH:19][CH:20]=2)[CH:15]=[CH:14]1)=[O:12])[CH3:9]

Participants

Conditions

Temperature: 0 °C

Procedure

Tetrahydrofuran (20 ml) and triethylamine (2.70 ml, 19.4 mmol) were added to N1-ethyl-5-(2-amino-4-pyridyl)oxy-1H-1-indolecarboxamide (1.91 g, 6.45 mmol, Production example 27-1); phenyl chloroformate (1.79 ml, 14.2 mmol) was added thereto at 0° C. while stirred; and the reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was partitioned between ethyl acetate and water; the organic layer was concentrated to yield a mixture (2.95 g) of phenyl N-(4-(1-(ethylamino)carbonyl-1H-5-indolyl)oxy-2-pyridyl)carbamate and phenyl N-(4-(1-(ethylamino)carbonyl-1H-5-indolyl)oxy-2-pyridyl)-N-(phenoxycarbonyl)carbamate. A portion of 0.454 g of the mixture was dissolved in N,N-dimethylformamide (5 ml); and 4-(1-pyrrolidinyl)piperidine (0.522 g, 3.39 mmol) was added; and the reaction mixture was stirred for 5 hours. The reaction mixture was partitioned between ethyl acetate and water; the organic layer was concentrated to yield a solid; the obtained solid was washed with hexane:diethyl ether=1:1 to yield the title compound as crystals (205 mg, 0.43 mmol). MS Spectrum (ESI): 477 (M+1), 953 (2M+1).

Workup

stirringand the reaction mixture was stirred at room temperature for 2 hours
customThe reaction mixture was partitioned between ethyl acetate and water
concentrationthe organic layer was concentrated

Sources & evidence

ORD record: ord-91ffe8db5ae742d9876967377e7e8c66
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07468380B2

Reaction notes

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