Triethylamine → N-tert-Butyl-3-((4-(4-(3-cyclobutylureido)benzoyl)piperazin-1-yl)methyl)-2-fluorobenzamide

HRID 1878406Notes

Reaction equation

Br[CH2:2][C:3]1[C:4]([F:16])=[C:5]([CH:13]=[CH:14][CH:15]=1)[C:6]([NH:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].[CH:17]1([NH:21][C:22]([NH:24][C:25]2[CH:30]=[CH:29][C:28]([C:31]([N:33]3[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]3)=[O:32])=[CH:27][CH:26]=2)=[O:23])[CH2:20][CH2:19][CH2:18]1.C(N(CC)CC)C>O1CCCC1>[C:9]([NH:8][C:6](=[O:7])[C:5]1[CH:13]=[CH:14][CH:15]=[C:3]([CH2:2][N:36]2[CH2:37][CH2:38][N:33]([C:31](=[O:32])[C:28]3[CH:29]=[CH:30][C:25]([NH:24][C:22]([NH:21][CH:17]4[CH2:18][CH2:19][CH2:20]4)=[O:23])=[CH:26][CH:27]=3)[CH2:34][CH2:35]2)[C:4]=1[F:16])([CH3:12])([CH3:11])[CH3:10]

Participants

Conditions

Temperature: 70 °C

Procedure

A stirred mixture of 3-(bromomethyl)-N-tert-butyl-2-fluorobenzamide (0.36 mmol, 105 mg), 1-cyclobutyl-3-(4-(piperazine-1-carbonyl)phenyl)urea (0.33 mmol, 620 mg) and triethylamine (2.5 mmol, 0.35 mL, 253 mg) in tetrahydrofuran (2 mL) was heated to 70° C. for 16 hours. After this time the volatiles were removed under vacuum. The residue was purified by strong cation exchange chromatography and basic reverse phase HPLC to yield the title compound (74 mg).

Workup

customAfter this time the volatiles were removed under vacuum
customThe residue was purified by strong cation exchange chromatography and basic reverse phase HPLC

Sources & evidence

ORD record: ord-05cce18f6aed401d92856d7f23e16f81
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08314091B2

Reaction notes

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