Triethylamine → HCID 25029152, compound

HRID 1644785Notes

Reaction equation

HRID 1644785 reaction equation
[F:1][C:2]([F:34])([F:33])[C:3]1[CH:4]=[C:5]([C@H:13]([O:16][C@H:17]2[CH2:25][CH2:24][C@H:23]3[C@@H:19]([CH2:20][NH:21][CH2:22]3)[C@@H:18]2[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[CH3:32])[CH2:14][OH:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[C:35](Cl)(=[O:39])[CH:36]([CH3:38])[CH3:37].C(N(CC)CC)C>C(Cl)Cl.CN(C1C=CN=CC=1)C>[F:10][C:9]([F:12])([F:11])[C:7]1[CH:6]=[C:5]([C@H:13]([O:16][C@H:17]2[CH2:25][CH2:24][C@H:23]3[C@@H:19]([CH2:20][N:21]([C:35](=[O:39])[CH:36]([CH3:38])[CH3:37])[CH2:22]3)[C@@H:18]2[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[CH3:32])[CH2:14][OH:15])[CH:4]=[C:3]([C:2]([F:33])([F:1])[F:34])[CH:8]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 62325Isobutyryl chlorideHCID 59293944HCID 59293944, compound

Product 1

HCID 25029152HCID 25029152, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of the compound from EXAMPLE 2 in CH2Cl2 was added isobutyric chloride, triethylamine and a catalytic amount of DMAP. The mixture was stirred at room temperature for 2 hr. The solvent was removed and the residue was heated with 10 mL 2 N NaOH in 40 mL methanol at 50° C. for 1 hr. Methanol was removed under vacuum. The residue was diluted with water and the aqueous was extracted with ethyl acetate. The organic layer was washed with brine, dried (MgSO4) and the solvent was removed. The residue was purified by preparative TLC (80:20 EtOAc:hexane), 0.07 mg. M++1: 558.16.

Workup

  1. customThe solvent was removed
  2. temperaturethe residue was heated with 10 mL 2 N NaOH in 40 mL methanol at 50° C. for 1 hr
  3. customMethanol was removed under vacuum
  4. additionThe residue was diluted with water
  5. extractionthe aqueous was extracted with ethyl acetate
  6. washThe organic layer was washed with brine
  7. dry with materialdried (MgSO4)
  8. customthe solvent was removed
  9. customThe residue was purified by preparative TLC (80:20 EtOAc:hexane), 0.07 mg

Sources & evidence

ORD record
ord-1fcee50b748a44bd9f54fc3356ea0ce9
Source dataset
uspto-grants-2012_02
Patent number
US08124633B2

Reaction notes

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