Methylamine → 4-(3-[(2S)-1-(1H-benzo[d]imidazol-2-ylsulfonyl)-2-piperidyl]-1,2,4-oxadiazol-5-ylmethoxy)benzylamine

HRID 397628Notes

Reaction equation

HRID 397628 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[S:10]([N:13]1[CH2:18][CH2:17][CH2:16][CH2:15][C@H:14]1[C:19]1[N:23]=[C:22]([CH2:24][O:25][C:26]2[CH:43]=[CH:42][C:29]([CH2:30][N:31]3C(=O)C4C(=CC=CC=4)C3=O)=[CH:28][CH:27]=2)[O:21][N:20]=1)(=[O:12])=[O:11].CN>C(O)C>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[S:10]([N:13]1[CH2:18][CH2:17][CH2:16][CH2:15][C@H:14]1[C:19]1[N:23]=[C:22]([CH2:24][O:25][C:26]2[CH:27]=[CH:28][C:29]([CH2:30][NH2:31])=[CH:42][CH:43]=2)[O:21][N:20]=1)(=[O:12])=[O:11]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 572671142-[4-(3-[(2S)-1-(1H-benzo[d]imidazol-2-ylsulfonyl)-2-piperidyl]-1,2,4-oxadiazol-5-ylmethoxy)benzyl]-1,3-isoindolinedione

Product 1

HCID 98258704-(3-[(2S)-1-(1H-benzo[d]imidazol-2-ylsulfonyl)-2-piperidyl]-1,2,4-oxadiazol-5-ylmethoxy)benzylamineYield 53.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-[4-(3-[(2S)-1-(1H-benzo[d]imidazol-2-ylsulfonyl)-2-piperidyl]-1,2,4-oxadiazol-5-ylmethoxy)benzyl]-1,3-isoindolinedione (885 mg) [see Example 10] was added to a solution of 33% w/w methylamine in ethanol (2.2 ml). The reaction mixture was stirred at room temperature for 5 hours after which time the solvent was removed under reduced pressure. The resulting solid was dissolved in 1N aqueous hydrochloric acid solution and dichloromethane. The aqueous layer was then separated and basified to pH 12 with 0.88 aqueous ammonia solution. The mixture was then extracted with ethyl acetate, the organic layer dried over magnesium sulphate and the solvent removed under reduced pressure to afford 4-(3-[(2S)-1-(1H-benzo[d]imidazol-2-ylsulfonyl)-2-piperidyl]-1,2,4-oxadiazol-5-ylmethoxy)benzylamine (369 mg) as a white solid.

Workup

  1. customwas removed under reduced pressure
  2. dissolutionThe resulting solid was dissolved in 1N aqueous hydrochloric acid solution
  3. customThe aqueous layer was then separated
  4. extractionThe mixture was then extracted with ethyl acetate
  5. dry with materialthe organic layer dried over magnesium sulphate
  6. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-895e0ca5c20f4c769382070de098e329
Source dataset
uspto-grants-2003_08
Patent number
US06610707B1

Reaction notes

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