Sodium Sulfate → HCID 11539062, compound

HRID 1767031Notes

Reaction equation

HRID 1767031 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.[C:15]([C:19]1[S:23][C:22]([NH:24][C:25](=[O:31])[CH:26]([NH2:30])[CH2:27][CH2:28][CH3:29])=[N:21][N:20]=1)([CH3:18])([CH3:17])[CH3:16].S([O-])([O-])(=O)=O.[Na+].[Na+].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl.C(O)(=O)C.C(N(CC)CC)C>[C:15]([C:19]1[S:23][C:22]([NH:24][C:25](=[O:31])[C@@H:26]([NH:30][CH:7]2[CH2:6][CH2:5][C:4]3[C:9](=[C:10]([F:12])[CH:11]=[C:2]([F:1])[CH:3]=3)[CH2:8]2)[CH2:27][CH2:28][CH3:29])=[N:21][N:20]=1)([CH3:17])([CH3:16])[CH3:18]

Participants

8

Reactant 4

HCID 24436Sodium SulfateHCID 40764316,8-Difluoro-2-tetraloneHCID 5049666Sodium triacetoxyborohydrideHCID 119279900HCID 119279900, compound

Product 1

HCID 11539062HCID 11539062, compoundYield 76.2%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of 6,8-difluoro-3,4-dihydro-1H-naphthalen-2-one (182 mg, 1.0 mmol), 2-amino-pentanoic acid (5-tert-butyl-[1,3,4]thiadiazol-2-yl)-amide HCl (293 mg, 1.0 mmol) in methylene chloride (25 mL) was treated with triethyl amine (0.14 mL), then acetic acid (0.27 mL) and sodium sulfate. After stirring for 15 min, 95% pure sodium triacetoxy borohydride (424 mg, 2.0 mmol) was added and the resulting mixture was stirred at rt overnight. The mixture was quenched with dilute water and extracted with methylene chloride. The organic layer was washed with dilute sodium bicarbonate to pH 8, separated, dried and concentrated to give 322 mg of the title compound as a yellow glass foam, LC-MS, RT=2.2 min, M+1=423.0. The glass foam was purified by HPLC to give the trifluoroacetic acid salt of the title compound as a brown solid, LC-MS, RT=2.3 min, M+1=423.0.

Workup

  1. stirringthe resulting mixture was stirred at rt overnight
  2. customThe mixture was quenched with dilute water
  3. extractionextracted with methylene chloride
  4. washThe organic layer was washed with dilute sodium bicarbonate to pH 8
  5. customseparated
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-5f6e3234033c42e3b0d5dbecb22b1bb9
Source dataset
uspto-grants-2007_06
Patent number
US07232820B2

Reaction notes

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