Dimethyl Sulfoxide → HCID 42634923, compound

HRID 445345Notes

Reaction equation

HRID 445345 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.[Cl:21][C:22]1[N:27]=[CH:26][C:25]([NH:28][C:29](=O)[O:30]C2C=CC([N+]([O-])=O)=CC=2)=[CH:24][CH:23]=1.CS(C)=O>C1(C)C=CC=CC=1>[Cl:21][C:22]1[N:27]=[CH:26][C:25]([NH:28][C:29]([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:30])=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 28293305(R)-1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinolineHCID 59536395HCID 59536395, compound

Product 1

HCID 42634923HCID 42634923, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of (R)-1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline (50 mg, 180 μmol, example 87, Step 3) and 4-nitrophenyl 6-chloropyridin-3-yl-carbamate (119 mg, 406 μmol) in toluene (1.0 mL) was subjected to a microwave irradiation at 180° C. for 30 min. Then, DMSO (1.0 mL) was added and the solution mixture was filtered. The filtrate was then purified by preparative HPLC (0%-100% MeCN 0.1% TFA/H2O 0.1% TFA) to give the title compound, which was dissolved in MeOH (1.0 mL). Then, the solution was washed through PL-HCO3 MP-Resin (200 mg per 6 mL tube) and the resin was washed with MeOH (2×0.3 mL). The combined washings were concentrated and dried under vacuum to give the title compound as a light yellow solid. MS (ESI, positive ion) m/z: 432 (M+H).

Workup

  1. filtrationthe solution mixture was filtered
  2. customThe filtrate was then purified by preparative HPLC (0%-100% MeCN 0.1% TFA/H2O 0.1% TFA)

Sources & evidence

ORD record
ord-a083033025d6456ea708db63728655ae
Source dataset
uspto-grants-2013_07
Patent number
US08476297B2

Reaction notes

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