Triethylamine → HCID 19745901, compound

HRID 1029446Notes

Reaction equation

HRID 1029446 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.[I-].ClC1C=CC=C[N+]=1C>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

6

Reactant 3

HCID 8471TriethylamineHCID 1670692-Chloro-1-methylpyridinium iodideHCID 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-chloro-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 (×2) 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 (×2) 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-cd962b93b2dc4eccb31ad0d7693e765f
Source dataset
uspto-grants-1992_04
Patent number
US05102881

Reaction notes

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