Acetic Acid → Ammonia

HRID 397629Notes

Reaction equation

HRID 397629 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[NH:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]=[C:7]1[S:15]([N:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH:19]1[C:24]1[N:28]=[C:27]([CH2:29][O:30][C:31]2[CH:38]=[CH:37][C:34]([CH:35]=O)=[CH:33][CH:32]=2)[O:26][N:25]=1)(=[O:17])=[O:16].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>O1CCCC1>[NH3:1].[NH:8]1[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N:6]=[C:7]1[S:15]([N:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH:19]1[C:24]1[N:28]=[C:27]([CH2:29][O:30][C:31]2[CH:38]=[CH:37][C:34]([CH2:35][N:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)=[CH:33][CH:32]=2)[O:26][N:25]=1)(=[O:16])=[O:17]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 31268PyrrolidineHCID 5049666Sodium triacetoxyborohydride2×HCID 23000729HCID 23000729, compound

Product 2

HCID 222AmmoniaHCID 9958389HCID 9958389, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Pyrrolidine (19 μl) was added to a solution of 4-(3-[1-(1H-benzo[d]imidazol-2-ylsulfonyl)-2-piperidyl]-1,2,4-oxadiazol-5-ylmethoxy)benzaldehyde (85 mg) [see Preparation 22] in tetrahydrofuran (10 ml). Sodium triacetoxyborohydride (64 mg) was added followed by glacial acetic acid (11.5 μl). The reaction mixture was stirred under an atmosphere of nitrogen for 6 hours. Sodium triacetoxyborohydride (21 mg) was added and the mixture was stirred for 56 hours after which time the solvent was removed under reduced pressure. The crude product was purified by column chromatography on silica gel eluting with a solvent gradient of 97.5:2.5:0.25 changing to 95:5:0.5, by volume, dichloromethane:methanol:0.88 aqueous ammonia solution to afford 3-[1-(1H-benzo[d]imidazol-2-ylsulfonyl)-2-piperidyl]-5-[4-(1-pyrrolidylmethyl)phenoxy]methyl-1,2,4-oxadiazole (90 mg) as a white solid.

Workup

  1. stirringthe mixture was stirred for 56 hours after which time the solvent
  2. customwas removed under reduced pressure
  3. customThe crude product was purified by column chromatography on silica gel eluting with a solvent gradient of 97.5:2.5:0.25 changing to 95:5:0.5, by volume, dichloromethane

Sources & evidence

ORD record
ord-0c476cbef6374c8aac195456ea0d2f97
Source dataset
uspto-grants-2003_08
Patent number
US06610707B1

Reaction notes

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