Diethyl Ether → HCID 11570827, compound

HRID 1984583Notes

Reaction equation

[CH2:1]([NH2:4])[CH2:2][CH3:3].[Cl:5][C:6]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:7]=1[S:13]([NH:16][C:17]1[N:22]=[C:21](Cl)[C:20]([S:24][C:25]2[CH:30]=[CH:29][C:28]([S:31]([N:34]3[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]3)(=[O:33])=[O:32])=[CH:27][CH:26]=2)=[CH:19][N:18]=1)(=[O:15])=[O:14].CCOCC>C1COCC1>[Cl:5][C:6]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:7]=1[S:13]([NH:16][C:17]1[N:22]=[C:21]([NH:4][CH2:1][CH2:2][CH3:3])[C:20]([S:24][C:25]2[CH:30]=[CH:29][C:28]([S:31]([N:34]3[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39]3)(=[O:33])=[O:32])=[CH:27][CH:26]=2)=[CH:19][N:18]=1)(=[O:14])=[O:15]

Participants

Conditions

Temperature: 50 °C

Procedure

n-Propylamine (25 mg, 0.42 mmol) was added to a solution of 11 (50 mg, 0.08 mmol) in THF (5 mL) and the mixture was stirred at 50° C. for 2 hours. The solution was cooled to room temperature, filtered and the precipitate was washed with THF. The filtrate was concentrated under reduced pressure to afford a yellow oil. Trituration with ether gave a solid which was purified by flash column chromatography (2% MeOH in DCM) to afford 12 as a white solid (28 mg). 1H NMR (DMSO): δ 0.54 (t, 3H), 1.22 (q, 2H), 1.33-1.34 (m, 2H), 1.51 (quin, 4H), 2.80-2.84 (m, 6H), 7.32 (d, 2H), 7.56 (d, 1H), 7.58 (d, 2H), 7.70 (s, 1H), 7.97 (br s, 1H), 8.07 (d, 1H), 8.15, (s, 1H) ppm. Mass Spectrum m/e=618.0 (M+1)

Workup

temperatureThe solution was cooled to room temperature
filtrationfiltered
washthe precipitate was washed with THF
concentrationThe filtrate was concentrated under reduced pressure
customto afford a yellow oil
customwas purified by flash column chromatography (2% MeOH in DCM)

Sources & evidence

ORD record: ord-da56cd32569047c2839866d5adc3fac1
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07544702B2

Reaction notes

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