Triethylamine → 7-Chloro-2-(4-methoxyphenylthiocarbamoyl)-6-phenyl-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-8-carboxylic acid amide

HRID 857887Notes

Reaction equation

HRID 857887 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[C:10]([C:24]([NH2:26])=[O:25])=[C:11]2[CH2:16][NH:15][CH2:14][CH2:13][N:12]2[C:17]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(N(CC)CC)C.[CH3:34][O:35][C:36]1[CH:41]=[CH:40][C:39]([N:42]=[C:43]=[S:44])=[CH:38][CH:37]=1>ClCCl>[Cl:8][C:9]1[C:10]([C:24]([NH2:26])=[O:25])=[C:11]2[CH2:16][N:15]([C:43](=[S:44])[NH:42][C:39]3[CH:38]=[CH:37][C:36]([O:35][CH3:34])=[CH:41][CH:40]=3)[CH2:14][CH2:13][N:12]2[C:17]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 752934-Methoxyphenyl isothiocyanateHCID 68886670HCID 68886670, compound

Product 1

HCID 589881127-Chloro-2-(4-methoxyphenylthiocarbamoyl)-6-phenyl-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-8-carboxylic acid amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A suspension of 7-chloro-6-phenyl-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-8-carboxylic acid amide trifluoroacetic acid salt (50 mg, Reference Example 1) in dry dichloromethane (5 mL) was treated with dry triethylamine (54 μL), then with a solution of 4-methoxyphenyl isothiocyanate (18 μL) in dry dichloromethane (5 mL). After stirring at room temperature for a further 3 hours the reaction mixture was further treated with dichloromethane (10 mL) and then washed three times with water (5 mL). The organic phase was dried over magnesium sulfate and evaporated. The residue was subjected to column chromatography on silica eluting with a mixture of pentane and ethyl acetate (1:1, v/v) to give 7-chloro-2-(4-methoxyphenylthiocarbamoyl)-6-phenyl-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-8-carboxylic acid amide (40 mg) as a white solid, m.p. 176–178° C. MS: 443 [MH]+, 441 [MH]+.

Workup

  1. washwashed three times with water (5 mL)
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. customevaporated
  4. additionThe residue was subjected to column chromatography on silica eluting with a mixture of pentane and ethyl acetate (1:1

Sources & evidence

ORD record
ord-d00df840b6264ca99aa4e5de2dc2d1d7
Source dataset
uspto-grants-2006_12
Patent number
US07148215B2

Reaction notes

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