Carbamic acid, 4-pyridinyl-, 4-nitrophenyl ester → (R)-N-(Pyridin-4-yl)-1-(4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2(1H)-carboxamide

HRID 445277

Reaction equation

[F:1][C:2]([F:20])([F:19])[C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12][CH2:11][NH:10]2)=[CH:5][CH:4]=1.[N:21]1[CH:26]=[CH:25][C:24]([NH:27][C:28](=O)[O:29]C2C=CC([N+]([O-])=O)=CC=2)=[CH:23][CH:22]=1>CC#N>[N:21]1[CH:26]=[CH:25][C:24]([NH:27][C:28]([N:10]2[CH2:11][CH2:12][C:13]3[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=3)[C@H:9]2[C:6]2[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:19])[F:20])=[CH:8][CH:7]=2)=[O:29])=[CH:23][CH:22]=1

Participants

Conditions

Temperature: 55 °C

Procedure

To a solution of (R)-1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline (200 mg, 0.721 mmol) in MeCN (3 mL) was added 4-nitrophenyl pyridin-4-ylcarbamate (561 mg, 2.164 mmol). The resulting mixture was heated to 55° C. overnight. After cooling down to RT the white precipitated obtained was filtered off and washed with DCM (2×1 mL). The combined filtrates were then concentrated and the residue purified by silica gel flash column chromatography (0%-100% EtOAc/hexane) to give the title compound as a white solid. MS (ESI, positive ion) m/z: 398 (M+H).

Workup

temperatureAfter cooling down to RT the
customwhite precipitated
customobtained
filtrationwas filtered off
washwashed with DCM (2×1 mL)
concentrationThe combined filtrates were then concentrated
customthe residue purified by silica gel flash column chromatography (0%-100% EtOAc/hexane)

Sources & evidence

ORD record: ord-52b057d0de864447b934fff0ed6b9904
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08476297B2

Linked notes

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