Diisopropylethylamine → 8-Fluoro-11-[3-(3-methoxy-propyl)-piperazin-1-yl]-2-trifluoromethyl-5h-dibenzo[b,e][1,4]diazepine

HRID 131422Notes

Reaction equation

Cl.[F:2][C:3]1[CH:4]=[CH:5][C:6]2[NH:12][C:11]3[CH:13]=[CH:14][C:15]([C:17]([F:20])([F:19])[F:18])=[CH:16][C:10]=3[C:9]([NH2:21])=[N:8][C:7]=2[CH:22]=1.[CH3:23][O:24][CH2:25][CH2:26][CH2:27][C@H:28]1[CH2:33]N[CH2:31][CH2:30][NH:29]1.C(N(C(C)C)CC)(C)C>C1(C)C=CC=CC=1.CS(C)=O>[F:2][C:3]1[CH:4]=[CH:5][C:6]2[NH:12][C:11]3[CH:13]=[CH:14][C:15]([C:17]([F:18])([F:20])[F:19])=[CH:16][C:10]=3[C:9]([N:21]3[CH2:31][CH2:30][NH:29][CH:28]([CH2:27][CH2:26][CH2:25][O:24][CH3:23])[CH2:33]3)=[N:8][C:7]=2[CH:22]=1

Participants

Conditions

Temperature: 110 °C

Procedure

Combine 8-fluoro-2-trifluoromethyl-5H-dibenzo[b,e][1,4]diazepin-11-ylaminehydrochloride (0.201 g, 0.606 mmol), (S)-2-(3-methoxy-propyl)-piperazine (0.192 g, 1.21 mmol), and diisopropylethyl amine (0.106 mL, 0.606 mmol) in a mixture of toluene (3 mL) and dimethylsulfoxide (1 mL) and stir at 110° C. for 24 hours. Evaporate the mixture then purify by flash chromatography, eluting with a step gradient starting with dichloromethane going to 7% 2N ammonia-methanol in dichloromethane gives 8-fluoro-11-[3-(3-methoxy-propyl)-piperazin-1-yl]-2-trifluoromethyl-5H-dibenzo[b,e][1,4]diazepine (0.151 g, 0.346 mmol, 57%) as a yellow oil. Mass spectrum (APCI): m/z=437.2 (M+1).

Workup

customEvaporate the mixture
customthen purify by flash chromatography
washeluting with a step gradient

Sources & evidence

ORD record: ord-359245cfb8764854b4e8974f47712079
Source dataset: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07384934B2

Reaction notes

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