Diisopropylethylamine → HCID 70557764, compound

HRID 1427160Notes

Reaction equation

HRID 1427160 reaction equation
[CH2:1]1[NH:6][CH2:5][CH2:4][N:3]2[C:7](=[O:14])[C:8]3[CH:13]=[N:12][CH:11]=[CH:10][C:9]=3[CH:2]12.CCN(C(C)C)C(C)C.[Br:24][C:25]1[CH:30]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:28]=[CH:27][C:26]=1[S:35](Cl)(=[O:37])=[O:36]>ClCCl>[Br:24][C:25]1[CH:30]=[C:29]([C:31]([F:33])([F:32])[F:34])[CH:28]=[CH:27][C:26]=1[S:35]([N:6]1[CH2:5][CH2:4][N:3]2[C:7](=[O:14])[C:8]3[CH:13]=[N:12][CH:11]=[CH:10][C:9]=3[CH:2]2[CH2:1]1)(=[O:37])=[O:36]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27786112-Bromo-4-(trifluoromethyl)benzenesulfonyl chlorideHCID 681762481,3,4,10b-Tetrahydropyrido[4',3':3,4]pyrrolo[1,2-a]pyrazin-6(2H)-one2×

Product 1

HCID 70557764HCID 70557764, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 1,3,4,10b-tetrahydropyrido[4′,3′:3,4]pyrrolo[1,2-a]pyrazin-6(2H)-one (may be prepared as in Intermediate 22, 90 mg) in dichloromethane (15 mL) was added DIPEA (0.415 mL). This was cooled in an ice bath and to this was added 2-bromo-4-(trifluoromethyl)benzenesulfonyl chloride (162 mg). The mixture was stirred at room temperature overnight. The reaction mixture was washed with aqueous saturated sodium bicarbonate solution in a hydrophobic frit and then re-extracted with DCM. The combined organic phases were evaporated to give the title compound as a yellow oil which was used in the next reaction (263 mg).

Workup

  1. temperatureThis was cooled in an ice bath
  2. washThe reaction mixture was washed with aqueous saturated sodium bicarbonate solution in a hydrophobic frit
  3. extractionre-extracted with DCM
  4. customThe combined organic phases were evaporated

Sources & evidence

ORD record
ord-91951c2de57f496fb33cbb6baada9a54
Source dataset
uspto-grants-2015_01
Patent number
US08933132B2

Reaction notes

Loading…