Triethylamine → HCID 67002825, compound

HRID 2362746Notes

Reaction equation

HRID 2362746 reaction equation
[Cl:1][C:2]1[C:3]([C:27]2[S:31][C:30]([C:32]3([OH:36])[CH2:35][O:34][CH2:33]3)=[N:29][CH:28]=2)=[C:4]2[CH:10]=[C:9]([C:11]3[CH2:12][CH2:13][NH:14][CH2:15][CH:16]=3)[N:8]([S:17]([C:20]3[CH:26]=[CH:25][C:23]([CH3:24])=[CH:22][CH:21]=3)(=[O:19])=[O:18])[C:5]2=[N:6][CH:7]=1.Cl[CH2:38][C:39]([N:41]([CH3:43])[CH3:42])=[O:40].C(N(CC)CC)C>CN1CCCC1=O>[Cl:1][C:2]1[C:3]([C:27]2[S:31][C:30]([C:32]3([OH:36])[CH2:35][O:34][CH2:33]3)=[N:29][CH:28]=2)=[C:4]2[CH:10]=[C:9]([C:11]3[CH2:12][CH2:13][N:14]([CH2:38][C:39]([N:41]([CH3:43])[CH3:42])=[O:40])[CH2:15][CH:16]=3)[N:8]([S:17]([C:20]3[CH:21]=[CH:22][C:23]([CH3:24])=[CH:25][CH:26]=3)(=[O:18])=[O:19])[C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 758862-chloro-N,N-dimethylacetamideHCID 67002767HCID 67002767, compound

Product 1

HCID 67002825HCID 67002825, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of Example 146C (0.047 g, 0.087 mmol), 2-chloro-N,N-dimethylacetamide (0.011 g, 0.091 mmol) and triethylamine (0.029 mL, 0.208 mmol) in 1-methyl-2-pyrrolidinone (0.8 mL) was heated to 75° C. for 1 hour. The reaction was cooled to ambient temperature and partitioned between water and ethyl acetate. The aqueous layer was extracted with additional ethyl acetate. The combined organic layers were washed with water (2×) and brine, dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was taken directly to the next step without further purification. MS ESI(+) m/z 628.2 [M+H]+.

Workup

  1. custompartitioned between water and ethyl acetate
  2. extractionThe aqueous layer was extracted with additional ethyl acetate
  3. washThe combined organic layers were washed with water (2×) and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was taken directly to the next step without further purification

Sources & evidence

ORD record
ord-80ceb3791c774b97a398049532b7b2a1
Source dataset
uspto-grants-2014_04
Patent number
US08691810B2

Reaction notes

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