Sodium Carbonate → HCID 70193430, compound

HRID 2186428Notes

Reaction equation

HRID 2186428 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[N:8]=[CH:9][N:10]([CH:12]([CH3:16])[CH2:13][CH:14]=O)[CH:11]=2)[CH:2]=1.[NH:17]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[NH2:18].C(=O)([O-])[O-].[Na+].[Na+]>CC(O)=O.O.CCOC(C)=O>[CH3:23][C:22]([O:21][C:19]([NH:17][NH:18][CH2:14][CH2:13][C@H:12]([N:10]1[CH:11]=[C:7]([C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)[N:8]=[CH:9]1)[CH3:16])=[O:20])([CH3:25])[CH3:24]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 70091tert-Butyl carbazateHCID 18759767β-Methyl-4-(3-pyridinyl)-1H-imidazole-1-propanal

Product 1

HCID 70193430HCID 70193430, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

(R/S)-3-(4-pyridin-3-yl-imidazol-1-yl)-butan-1-al (11) (1 mmol) is dissolved in 10 mL HOAc and t-butyl hydrazinecarboxylate (1.1 mmol) is added. After 1 h, NaHB(OAc)3 (5 mmol) is added at 25° C. After 2 h, the reaction is poured into sodium carbonate in water and EtOAc. The water layer is removed, the organics are washed with brine, and dried over sodium sulfate. The solvent is removed in vacuo to leave the product (32).

Workup

  1. waitAfter 2 h
  2. customThe water layer is removed
  3. washthe organics are washed with brine
  4. dry with materialdried over sodium sulfate
  5. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-ecf2ad3b1cd74d89a09ecf67779636c5
Source dataset
uspto-grants-2002_06
Patent number
US06403776B1

Reaction notes

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