Acetic Acid → HCID 11590159, compound

HRID 1767026Notes

Reaction equation

HRID 1767026 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([F:12])[CH:11]=1)[CH2:8][C:7](=O)[CH2:6][CH2:5]2.Cl.[NH2:15][CH:16]([CH2:31][CH3:32])[C:17]([NH:19][C:20]1[S:21][C:22]([C:25]([CH3:30])([CH3:29])[CH2:26][CH:27]=[CH2:28])=[N:23][N:24]=1)=[O:18].C(O)(=O)C.S([O-])([O-])(=O)=O.[Na+].[Na+].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl.O.C(=O)(O)[O-].[Na+].CCN(CC)CC>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([F:12])[CH:11]=1)[CH2:8][CH:7]([NH:15][C@@H:16]([CH2:31][CH3:32])[C:17]([NH:19][C:20]1[S:21][C:22]([C:25]([CH3:30])([CH3:29])[CH2:26][CH:27]=[CH2:28])=[N:23][N:24]=1)=[O:18])[CH2:6][CH2:5]2

Participants

10

Reactant 5

HCID 176Acetic AcidHCID 24436Sodium SulfateHCID 40764316,8-Difluoro-2-tetraloneHCID 5049666Sodium triacetoxyborohydrideHCID 69471052HCID 69471052, compound

Product 1

HCID 11590159HCID 11590159, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of 6,8-difluoro-3,4-dihydro-1H-naphthalen-2-one (182 mg, 1 mmol), 2-amino-N-[5-(1,1-dimethyl-but-3-enyl)-[1,3,4]thiadiazol-2-yl]-butyramide HCl (305 mg, 1.0 mmol), NEt3 (0.14 ml), acetic acid (0.27 ml, 4 mmol), sodium sulfate in methylene chloride was stirred at room temperature for 1 hr. 95% pure sodium triacetoxy borohydride (424 mg, 2.0 mmol) was added and the mixture was stirred at rt overnight. The mixture was diluted with dilute water, saturated sodium bicarbonate to pH 7-7.5 and extracted with methylene chloride. The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. The crude products were purified by silica gel column chromatography using methylene chloride to 10% methanol in methylene chloride as eluent to give the title compound as ayellow oil. LC-MS, RT=2.1 min, M+1=435.3. The corresponding HCl salt was prepared as a beige solid.

Workup

  1. stirringthe mixture was stirred at rt overnight
  2. extractionextracted with methylene chloride
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude products were purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a8285e2d1fb345ae90b239b5677e7542
Source dataset
uspto-grants-2007_06
Patent number
US07232820B2

Reaction notes

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