Hydrochloric Acid → HCID 57636761, compound

HRID 2110989Notes

Reaction equation

HRID 2110989 reaction equation
[F:1][C:2]1[C:11]2[O:10][CH2:9][C@H:8]3[C@@H:12]([NH:13][C:14]([NH:16][C:17]4[CH:22]=[CH:21][C:20]([C:23](=[O:31])[C:24]5[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=5)=[CH:19][N:18]=4)=[O:15])[C@H:7]3[C:6]=2[C:5]([F:32])=[CH:4][CH:3]=1.[BH4-].[Na+].Cl>CO.O>[F:1][C:2]1[C:11]2[O:10][CH2:9][C@H:8]3[C@@H:12]([NH:13][C:14]([NH:16][C:17]4[CH:22]=[CH:21][C:20]([CH:23]([C:24]5[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=5)[OH:31])=[CH:19][N:18]=4)=[O:15])[C@H:7]3[C:6]=2[C:5]([F:32])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 69055100N-[(1S,1aR,7bR)-4,7-difluoro-1,1a,2,7b-tetrahydro-cyclopropa[c]chromen-1-yl]-N'-[5-(4-fluorobenzoyl)-2-pyridinyl]urea

Product 1

HCID 57636761HCID 57636761, compoundYield 59.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

N-[(1S,1aR,7bR)-4,7-difluoro-1,1a,2,7b-tetrahydrocyclopropa[c]chromen-1-yl]-N′-[5-(4-fluorobenzoyl)-2-pyridinyl]urea (20 mg) was dissolved in methanol and sodium borohydride (appr. 20 mg) was added to the reaction mixture in small portions. The reaction mixture was stirred for about 3 h at ambient temperature. The reaction was monitored by TLC. The reaction mixture was diluted with water, acidified with 1N HCl and extracted into methylene chloride. Organic extract low as washed with water and bine, dried over magnesium sulfate and concentrated. Purification by column chromatography on silica (EtOAc/hexane) gave 12 mg of pure product.

Workup

  1. extractionextracted into methylene chloride
  2. extractionOrganic extract low
  3. washas washed with water and bine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customPurification by column chromatography on silica (EtOAc/hexane)

Sources & evidence

ORD record
ord-6328bbd9e7dd439395df53552238f55d
Source dataset
uspto-grants-2009_04
Patent number
US07517992B2

Reaction notes

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