4-Fluorophenyl isocyanate → HCID 59536350, compound

HRID 445329Notes

Reaction equation

HRID 445329 reaction equation
[CH3:1][C@H:2]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C@@H:4]([C:12]2[CH:20]=[CH:19][C:15]([C:16]([OH:18])=[O:17])=[CH:14][CH:13]=2)[NH:3]1.[F:21][C:22]1[CH:27]=[CH:26][C:25]([N:28]=[C:29]=[O:30])=[CH:24][CH:23]=1>C(Cl)Cl>[F:21][C:22]1[CH:27]=[CH:26][C:25]([NH:28][C:29]([N:3]2[C@@H:2]([CH3:1])[CH2:11][C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[C@H:4]2[C:12]2[CH:20]=[CH:19][C:15]([C:16]([OH:18])=[O:17])=[CH:14][CH:13]=2)=[O:30])=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 709554-Fluorophenyl isocyanateHCID 59536380HCID 59536380, compound

Product 1

HCID 59536350HCID 59536350, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-((1R,3S)-3-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl)benzoic acid (22 mg, 82 μmol) in CH2Cl2 (0.5 mL) at RT was added 1-fluoro-4-isocyanatobenzene (28 mg, 206 μmol). The reaction was stirred 5 h and directly purified by HPLC to give 4-((1R,3S)-2-((4-fluorophenyl)carbamoyl)-3-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl)benzoic acid as a white solid. MS (ESI pos. ion) m/z: 405 (M+1).

Workup

  1. customdirectly purified by HPLC

Sources & evidence

ORD record
ord-d0b69e7a6a614340bd2bd17c742bb2ed
Source dataset
uspto-grants-2013_07
Patent number
US08476297B2

Reaction notes

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