Triethylamine → HCID 25121261, compound

HRID 1640935Notes

Reaction equation

CS(Cl)(=O)=O.[N:6]1([CH2:11][CH2:12][NH:13][C:14]2[N:19]=[C:18]([C:20]3[S:24][C:23]4[C:25]([C:29]5[CH:34]=[C:33]([F:35])[N:32]=[CH:31][C:30]=5[CH:36](O)[CH3:37])=[CH:26][CH:27]=[CH:28][C:22]=4[CH:21]=3)[C:17]([F:39])=[CH:16][N:15]=2)[CH:10]=[CH:9][N:8]=[N:7]1.C(N(CC)CC)C.[CH:47]1([NH2:50])[CH2:49][CH2:48]1>C(Cl)Cl>[N:6]1([CH2:11][CH2:12][NH:13][C:14]2[N:19]=[C:18]([C:20]3[S:24][C:23]4[C:25]([C:29]5[C:30]([CH:36]([NH:50][CH:47]6[CH2:49][CH2:48]6)[CH3:37])=[CH:31][N:32]=[C:33]([F:35])[CH:34]=5)=[CH:26][CH:27]=[CH:28][C:22]=4[CH:21]=3)[C:17]([F:39])=[CH:16][N:15]=2)[CH:10]=[CH:9][N:8]=[N:7]1

Participants

Conditions

Temperature: 45 °C

Procedure

Slowly add methanesulfonyl chloride (0.04 mL, 0.55 mmol) to a solution of newly synthesized 1-(4-(2-(2-(2-(1H-1,2,3-triazol-1-yl)ethylamino)-5-fluoropyrimidin-4-yl)benzo[b]thiophen-7-yl)-6-fluoropyridin-3-yl)ethanol (240 mg, 0.50 mmol) and triethylamine (0.14 mL, 1.0 mmol) in methylene chloride (5 mL) at −78° C. After stirring the mixture at the same temperature for another 60 min, add cyclopropylamine (0.040 mL, 0.55 mmol) and leave it overnight at RT. Heat it to 45° C. for 5 h, cool to RT, and remove the solvent. Purify by column chromatography (10% methanol in DCM) to afford the title compound (42 mg 17%). MS (ES) m/z 519 [M+1]+.

Workup

customat −78° C
customleave it overnight at RT
temperaturecool to RT
customremove the solvent
customPurify by column chromatography (10% methanol in DCM)

Sources & evidence

ORD record: ord-aa3aefbaf1d34134aa55fac154358a18
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08114872B2

Reaction notes

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