Ammonia → HCID 59536352, compound

HRID 445266Notes

Reaction equation

HRID 445266 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:8]=[CH:7][C:6]([CH: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.[C:21](N1C=CN=C1)([N:23]1C=CN=C1)=[S:22].N>O1CCCC1>[F:20][C:2]([F:1])([F:19])[C:3]1[CH:4]=[CH:5][C:6]([CH:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12][CH2:11][N:10]2[C:21](=[S:22])[NH2:23])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 802641,1'-ThiocarbonyldiimidazoleHCID 166406961-(4-(Trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 59536352HCID 59536352, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline (0.5 g, 2 mmol) (Example 9, step 3) in dry tetrahydrofuran (10 mL) was treated with 1,1′-thiocarbonyldiimidazole (0.5 g, 3 mmol) and stirred at RT for 4 h. The solvent was removed and the resulting residue was dissolved in ammonia (2.0 M solution in methanol, 15 mL, 30 mmol) and stirred the resulting solution in a pressure tube at RT for 1 h followed by heating at 55° C. for 5 h. The solvent was removed under vacuum and the residue was purified by preparative HPLC [gradient 10-90% MeCN (0.1% TFA)/H2O (0.1% TFA)] to give 1-(4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2(1H)-carbothioamide as a white solid. MS (ESI, pos. ion) m/z: 337 (M+1).

Workup

  1. customThe solvent was removed
  2. stirringstirred the resulting solution in a pressure tube at RT for 1 h
  3. temperatureby heating at 55° C. for 5 h
  4. customThe solvent was removed under vacuum
  5. customthe residue was purified by preparative HPLC [gradient 10-90% MeCN (0.1% TFA)/H2O (0.1% TFA)]

Sources & evidence

ORD record
ord-9d55a1920c8344b082155f53a277aa2d
Source dataset
uspto-grants-2013_07
Patent number
US08476297B2

Reaction notes

Loading…