Dichloromethane → HCID 86761276, compound

HRID 1362905Notes

Reaction equation

HRID 1362905 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][C@H:11]([C:14]3[CH:19]=[C:18]([F:20])[C:17]([F:21])=[CH:16][C:15]=3[F:22])[C@@H:10]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH2:9]2)[CH:5]=[CH:4][C:3]=1[N+:31]([O-])=O.[BH4-].[Na+].C(Cl)Cl>CO.O1CCCC1.O.O.O.O.O.O.[Ni](Cl)Cl>[NH2:31][C:3]1[CH:4]=[CH:5][C:6]([N:8]2[CH2:13][CH2:12][C@H:11]([C:14]3[CH:19]=[C:18]([F:20])[C:17]([F:21])=[CH:16][C:15]=3[F:22])[C@@H:10]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:28])([CH3:27])[CH3:29])[CH2:9]2)=[N:7][C:2]=1[NH2:1]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 4311764Sodium borohydrideHCID 86761277HCID 86761277, compound

Product 1

HCID 86761276HCID 86761276, compound

Reagents, catalysts & solvents 2

HCID 11791229Dichloronickel;hexahydrateCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To 85 mg (0.18 mmol) of the product of Step A in 4 mL of 3:1 methanol/tetrahydrofuran at 0° C. was added 2.5 mg (0.01 mmol) of nickel (II) chloride hexahydrate followed by 40 mg (1.0 mmol) of sodium borohydride in four 10 mg portions every 5 min. The reaction mixture was stirred for an additional 10 min and poured into 20 mL of a 1:1 mixture of methylene chloride/saturated aqueous ammonium chloride solution. The layers were separated and the aqueous phase extracted with three 10-mL portions of methylene chloride. The combined organic phases were dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to yield a purple solid which was purified by preparative thin layer chromatography using an Analtech® 1500 micron plate (1:2 hexane/ethyl acetate solvent) to give the title compound as a purple crystalline solid. LC/MS 438.1 (M+1).

Workup

  1. customThe layers were separated
  2. extractionthe aqueous phase extracted with three 10-mL portions of methylene chloride
  3. dry with materialThe combined organic phases were dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customto yield a purple solid which
  7. customwas purified by preparative thin layer chromatography

Sources & evidence

ORD record
ord-28353875a48248bbba1522921aa6095c
Source dataset
uspto-grants-2011_02
Patent number
US07884104B2

Reaction notes

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