Triethylamine → HCID 19745901, compound

HRID 2253746Notes

Reaction equation

HRID 2253746 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH:10]([S:29][CH2:30][CH2:31][C:32](O)=[O:33])[C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]3[CH:28]=[CH:27][C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[N:20]=3)=[CH:13][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC[N:37](CC)CC>C(Cl)Cl.CC#N>[C:1]1([CH2:7][CH2:8][CH2:9][CH:10]([S:29][CH2:30][CH2:31][C:32]([NH2:37])=[O:33])[C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]3[CH:28]=[CH:27][C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[N:20]=3)=[CH:13][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 19745889HCID 19745889, compound

Product 1

HCID 19745901HCID 19745901, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of the title acid of Example 2 (200 mg) in CH2Cl2 (3 mL) and CH3CN (1 mL) at 0° C. was added Et3N (120 μL) followed by 2-chlorol-methylpyridinium iodide (220 mg). After stirring for 75 mins. at 0° C., an excess of NH3 was slowly bubbled into the mixture and the reaction was allowed to stir at RT for 12 h. It was then diluted with ethyl acetate and washed successively with aq. NH4OAc (x2) and brine. After drying, the organic solution was concentrated and the residue was purified on a column of silica to afford the title compound.

Workup

  1. customat 0° C., an excess of NH3 was slowly bubbled into the mixture
  2. stirringto stir at RT for 12 h
  3. additionIt was then diluted with ethyl acetate
  4. washwashed successively with aq. NH4OAc (x2) and brine
  5. customAfter drying
  6. concentrationthe organic solution was concentrated
  7. customthe residue was purified on a column of silica

Sources & evidence

ORD record
ord-8215c2e0d1994816a69611ed9ca84122
Source dataset
uspto-grants-1993_08
Patent number
US05232916

Reaction notes

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