Hydrazine → (R)-N-(2-aminoethyl)-N-(4-fluorophenyl)-1-(4-(trifluoromethyl)-phenyl)-3,4-dihydroisoquinoline-2(1H)-carboxamide

HRID 445380Notes

Reaction equation

HRID 445380 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[CH2:12][CH2:13][N:14]([C:37]1[CH:42]=[CH:41][C:40]([F:43])=[CH:39][CH:38]=1)[C:15]([N:17]1[CH2:26][CH2:25][C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C@H:18]1[C:27]1[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=1)=[O:16].NN>CCO>[NH2:3][CH2:12][CH2:13][N:14]([C:37]1[CH:38]=[CH:39][C:40]([F:43])=[CH:41][CH:42]=1)[C:15]([N:17]1[CH2:26][CH2:25][C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C@H:18]1[C:27]1[CH:32]=[CH:31][C:30]([C:33]([F:35])([F:34])[F:36])=[CH:29][CH:28]=1)=[O:16]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 59536256(R)-N-(2-(1,3-dioxoisoindolin-2-yl)ethyl)-N-(4-fluorophenyl)-1-(4-(trifluoromethyl)-phenyl)-3,4-dihydroisoquinoline-2(1H)-carboxamide

Product 1

HCID 59536372(R)-N-(2-aminoethyl)-N-(4-fluorophenyl)-1-(4-(trifluoromethyl)-phenyl)-3,4-dihydroisoquinoline-2(1H)-carboxamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a 50 mL round-bottomed flask was added (R)—N-(2-(1,3-dioxoisoindolin-2-yl)ethyl)-N-(4-fluorophenyl)-1-(4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2(1H)-carboxamide (16 mg, 27 μmol, from step 4), EtOH (1 mL), hydrazine, anhydrous (3.5 μL, 109 μmol, Aldrich). The solution was stirred at RT for 18 h. The solvent was removed in vacuo and the residue was purified by silica gel chromatography, eluting with 10% MeOH/CH2Cl2+1% ammonia (37% in water) to give (R)—N-(2-aminoethyl)-N-(4-fluorophenyl)-1-(4-(trifluoromethyl)-phenyl)-3,4-dihydroisoquinoline-2(1H)-carboxamide. MS (ESI pos. ion) m/z: 458 (M+1).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by silica gel chromatography
  3. washeluting with 10% MeOH/CH2Cl2+1% ammonia (37% in water)

Sources & evidence

ORD record
ord-d79cc9f349b54918bc8c858d7a60cb92
Source dataset
uspto-grants-2013_07
Patent number
US08476297B2

Reaction notes

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