Diisobutylaluminum hydride → HCID 15871315, compound

HRID 1871620Notes

Reaction equation

HRID 1871620 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]=2[Cl:18])[N:5]=[C:4]([S:19][CH3:20])[C:3]=1[C:21](=[O:35])[C:22]1[CH:27]=[C:26]([CH2:28][CH2:29][C:30](OC)=[O:31])[CH:25]=[CH:24][C:23]=1[CH3:34].CC(C[AlH]CC(C)C)C>C1COCC1>[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:17])([F:15])[F:16])=[CH:9][C:8]=2[Cl:18])[N:5]=[C:4]([S:19][CH3:20])[C:3]=1[C:21](=[O:35])[C:22]1[CH:27]=[C:26]([CH2:28][CH2:29][CH2:30][OH:31])[CH:25]=[CH:24][C:23]=1[CH3:34]

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 18427789HCID 18427789, compound

Product 1

HCID 15871315HCID 15871315, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 0.530 g (1.0 mmol) of 5-amino-1-(2,6-dichloro4-trifluoromethylphenyl)-4-(5-[β-methoxycarbonylethyl]-2-methylbenzoyl)-3-methylthiopyrazole in 10 mL of THF was cooled in an ice bath while 1.33 mL of a 1.5 M solution of DIBAL in THF was added. The reaction mixture was warmed to room temperature and then quenched with water. The product was extracted into EtOAc, dried and concentrated. The residues were chromatographed on silica gel using mixtures of hexane/EtOAc to elute the title product which was isolated as an amorphous foam, 174 mg (34%). Anal. Calcd. for C22H20O2N3SCl2F3 : C, 50.97; H, 3.88; N, 8.10. Found, C, 51.10; H, 3.96; N, 7.60.

Workup

  1. additionwas added
  2. customquenched with water
  3. extractionThe product was extracted into EtOAc
  4. customdried
  5. concentrationconcentrated
  6. customThe residues were chromatographed on silica gel using mixtures of hexane/EtOAc
  7. washto elute the title product which
  8. customwas isolated as an amorphous foam, 174 mg (34%)

Sources & evidence

ORD record
ord-cd56d37a7a9d4d27b89752d30c08e716
Source dataset
uspto-grants-2000_08
Patent number
US06103900

Reaction notes

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