Water → HCID 44218579, compound

HRID 1931499Notes

Reaction equation

[C@H:1]1([NH:10][C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16]([NH2:21])[CH:17]=3)[N:12]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.Cl[C:23]([O:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=1)=[O:24].C(N(CC)CC)C.O>C1(C)C=CC=CC=1>[CH3:33][O:32][C:29]1[CH:30]=[CH:31][C:26]([O:25][C:23](=[O:24])[NH:21][C:16]2[CH:17]=[C:18]3[C:13](=[CH:14][CH:15]=2)[N:12]=[C:11]([NH:10][C@H:1]2[C:9]4[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=4)[CH2:3][CH2:2]2)[CH:20]=[CH:19]3)=[CH:27][CH:28]=1

Participants

Conditions

Temperature: 60 °C

Procedure

(R)—N2-Indan-1-yl-quinoline-2,6-diamine (0.070 g, 0.25 mmol) was dissolved in toluene (3 ml). 4-Methoxyphenyl chloroformate (0.042 mL, 0.28 mmol) and triethyl amine (0.053 mL, 0.38 mmol) were added and the reaction mixture was stirred at 60° C. for 10 h. Water (20 mL) was added and the mixture was extracted with ethyl acetate (3×15 mL). The combined organic phases were dried on sodium sulfate, filtered and the filtrate was evaporated. The crude product was purified by column chromatography (silica gel, heptane/ethyl acetate 4:1=>2:1) to yield the title compound as a colorless solid (33 mg, 31%); MS: m/e=326.6 (M+H+).

Workup

extractionthe mixture was extracted with ethyl acetate (3×15 mL)
customThe combined organic phases were dried on sodium sulfate
filtrationfiltered
customthe filtrate was evaporated
customThe crude product was purified by column chromatography (silica gel, heptane/ethyl acetate 4:1=>2:1)

Sources & evidence

ORD record: ord-d86e11c02bac4e8f95f4f242ca925c30
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188284B2

Reaction notes

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