Dichloromethane → HCID 66823227, compound

HRID 331684Notes

Reaction equation

HRID 331684 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[CH2:11]([CH:18]([C:39]#[N:40])[C:19]1[CH:20]=[C:21]([CH:35]=[CH:36][C:37]=1[F:38])[O:22][CH2:23][CH2:24][NH:25][S:26]([C:29]1[N:30]=[CH:31][N:32]([CH3:34])[CH:33]=1)(=[O:28])=[O:27])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[BH4-].[Na+].[OH-].[Na+].[Cl:45]CCl>C1(C)C=CC=CC=1.O1CCCC1.CO>[ClH:45].[NH2:40][CH2:39][CH:18]([C:19]1[CH:20]=[C:21]([CH:35]=[CH:36][C:37]=1[F:38])[O:22][CH2:23][CH2:24][NH:25][S:26]([C:29]1[N:30]=[CH:31][N:32]([CH3:34])[CH:33]=1)(=[O:28])=[O:27])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

8

Reactant 5

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 21225700DiisobutylaluminumhydrideHCID 66823139HCID 66823139, compound

Product 1

HCID 66823227HCID 66823227, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A 1M solution of diisobutylaluminium hydride (3.53 ml, 3.53 mmol) in toluene was added dropwise to a solution of 1-methyl-1H-imidazole-4-sulfonic acid {2-[3-(benzyl-cyanomethyl)-4-fluoro-phenoxy]-ethyl}-amide (721 mg, 1.683 mmol) in 4 ml dichloromethane at 0° C. The reaction was stirred at this temperature for 30 min and then added to a suspension of sodium borohydride (2546 mg, 67.3 mmol) in 5 ml tetrahydrofuran/methanol (1:3) at 0° C., stirred for 1 h allowing to warm up to room temperature. 1 N sodium hydroxide solution was added and the mixture was extracted three times with dichloromethane. The combined organic layers were washed with water and brine, dried over sodium sulfate, filtered and evaporated to obtain the free amine as a white solid which was purified by flash chromatography on SiO2 cartridge (10% methanol in dichloromethane) to obtain 285 mg (36%) product as a colourless solid.

Workup

  1. stirringstirred for 1 h
  2. extractionthe mixture was extracted three times with dichloromethane
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-cde96cec0b8a427fafe7abfcc466a503
Source dataset
uspto-grants-2014_11
Patent number
US08877794B2

Reaction notes

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