Dichloromethane → HCID 66823227, compound

HRID 591182Notes

Reaction equation

HRID 591182 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-cyano-methyl)-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-d7607f59adf24021a1ffc09fd0cc6a46
Source dataset
uspto-grants-2016_01
Patent number
US09238619B2

Reaction notes

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