Triethylamine → HCID 68888150, compound

HRID 857883Notes

Reaction equation

HRID 857883 reaction equation
FC(F)(F)C(O)=O.[C:8]([C:10]1[C:11]([C:22]([NH2:24])=[O:23])=[C:12]2[CH2:17][NH:16][CH2:15][CH2:14][N:13]2[C:18]=1[CH:19]1[CH2:21][CH2:20]1)#[N:9].C(N(CC)CC)C.[F:32][C:33]([F:45])([F:44])[C:34]1[CH:39]=[CH:38][C:37]([S:40](Cl)(=[O:42])=[O:41])=[CH:36][CH:35]=1>C(#N)C>[C:8]([C:10]1[C:11]([C:22]([NH2:24])=[O:23])=[C:12]2[CH2:17][N:16]([S:40]([C:37]3[CH:36]=[CH:35][C:34]([C:33]([F:32])([F:44])[F:45])=[CH:39][CH:38]=3)(=[O:42])=[O:41])[CH2:15][CH2:14][N:13]2[C:18]=1[CH:19]1[CH2:20][CH2:21]1)#[N:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27773994-(Trifluoromethyl)benzenesulfonyl chlorideHCID 68887591HCID 68887591, compound

Product 1

HCID 68888150HCID 68888150, compoundYield 42.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

A suspension of 7-cyano-6-cyclopropyl-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-8-carboxylic acid amide trifluoroacetic acid salt [200 mg, Example 44(b)] in dry acetonitrile (50 mL) was treated with dry triethylamine (0.16 mL), then with 4-(trifluoromethyl)benzenesulfonyl chloride (142 mg). After stirring at 60° C. for 2.5 hours the reaction mixture was allowed to cool to room temperature and evaporated. The residue was treated with ethyl acetate (40 mL) and water (40 ml). The organic phase was separated, dried over sodium sulfate and evaporated. The residue was subjected to column chromatography on silica eluting with a mixture of ethyl acetate and pentane (1:1, v/v) to give 7-Cyano-6-cyclopropyl-2-(4-trifluoromethylbenzenesulfonyl)-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-8-carboxylic acid amide (109 mg) as a white solid, m.p. 253–256° C.

Workup

  1. temperatureto cool to room temperature
  2. customevaporated
  3. additionThe residue was treated with ethyl acetate (40 mL) and water (40 ml)
  4. customThe organic phase was separated
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. additionThe residue was subjected to column chromatography on silica eluting with a mixture of ethyl acetate and pentane (1:1

Sources & evidence

ORD record
ord-b8e60774fdd64a54855029616196745c
Source dataset
uspto-grants-2006_12
Patent number
US07148215B2

Reaction notes

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