Tetrahydrofuran → HCID 86670950, compound

HRID 515304Notes

Reaction equation

[NH2:1][C:2]1[C:31]([F:32])=[CH:30][C:5]([CH2:6][CH:7]2[CH2:12][CH2:11][N:10]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]([OH:29])([C:25]([F:28])([F:27])[F:26])[C:21]([F:24])([F:23])[F:22])=[CH:16][CH:15]=3)[CH2:9][CH2:8]2)=[C:4]([Cl:33])[CH:3]=1.C(Cl)(=O)OC1C=CC([N+:42]([O-])=O)=CC=1.[NH2:47][CH2:48][C:49]([CH3:52])(O)[CH3:50].[O:53]1[CH2:57]CCC1>>[NH2:42][C:49]([CH3:52])([CH3:50])[CH2:48][NH:47][C:57]([NH:1][C:2]1[CH:3]=[C:4]([Cl:33])[C:5]([CH2:6][CH:7]2[CH2:12][CH2:11][N:10]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]([OH:29])([C:25]([F:28])([F:26])[F:27])[C:21]([F:22])([F:23])[F:24])=[CH:16][CH:15]=3)[CH2:9][CH2:8]2)=[CH:30][C:31]=1[F:32])=[O:53]

Participants

Reactant 4

HCID 8028Tetrahydrofuran

HCID 821294-Nitrophenyl chloroformate

HCID 951022-Propanol, 1-amino-2-methyl-

HCID 86670951HCID 86670951, compound

Product 1

HCID 86670950HCID 86670950, compound

Procedure

A solution of 2-(4-((4-(4-amino-2-chloro-5-fluorobenzyl)piperidin-1-yl)methyl)phenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (0.200 mmol, 100 mg) and 4-nitrophenyl carbonochloridate (0.200 mmol, 40.4 mg) in tetrahydrofuran (5 mL) was stirred at room temperature for 30 minutes. 1-Amino-2-methylpropan-2-ol (0.401 mmol, 0.051 mL, 35.7 mg) was added and the reaction was kept at room temperature overnight. The reaction mixture was concentrated under vacuum and residue purified by silica column chromatography (eluent: dichloromethane-5% methanol in dichloromethane) to afford the title compound (58.5 mg). MS (ESI) m/z 614.1 [M+H]+

Workup

concentrationThe reaction mixture was concentrated under vacuum and residue
custompurified by silica column chromatography (eluent: dichloromethane-5% methanol in dichloromethane)

Sources & evidence

ORD record: ord-c50a77e36d7d4c25986ec8336b062561
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09108939B2

Reaction notes

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