Triethylamine → HCID 11976665, compound

HRID 854268Notes

Reaction equation

HRID 854268 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][C:5]1[N:10]=[C:9]([CH:11]([C:14]2[S:15][C:16]3[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=3[N:18]=2)[C:12]#[N:13])[CH:8]=[CH:7][N:6]=1.[Cl:23][C:24]1[CH:32]=[CH:31][C:27]([C:28](Cl)=[O:29])=[CH:26][CH:25]=1.C(N(CC)CC)C>C(Cl)Cl.CN(CC1C=C(CN(C)C)C(O)=C(CN(C)C)C=1)C>[S:15]1[C:16]2[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=2[N:18]=[C:14]1[CH:11]([C:12]#[N:13])[C:9]1[CH:8]=[CH:7][N:6]=[C:5]([NH:4][CH2:3][CH2:2][NH:1][C:28](=[O:29])[C:27]2[CH:31]=[CH:32][C:24]([Cl:23])=[CH:25][CH:26]=2)[N:10]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 85014-Chlorobenzoyl chlorideHCID 11278325HCID 11278325, compound

Product 1

HCID 11976665HCID 11976665, compoundYield 68.2%

Reagents, catalysts & solvents 1

HCID 131726551HCID 131726551, compoundSolvent

Procedure

To a solution of 46 (0.1 g, 0.32 mmol) in DCM/DMF 3/1 (4 ml) was added p-chloro benzoylchloride (0.056 g, 0.32 mmol) and triethylamine (0.09 ml, 0.64 mmol) and the solution was shaken overnight at r.t then at 40° C. for 3 h. After cooling down to r.t, the precipitate formed was filtered off then washed with DCM then water. After recrystallization in acetonitrile, 98 mg (68%) of the title compound (base) was obtained as a yellow powder.

Workup

  1. waitat 40° C. for 3 h
  2. temperatureAfter cooling down
  3. customthe precipitate formed
  4. filtrationwas filtered off
  5. washthen washed with DCM
  6. customAfter recrystallization in acetonitrile

Sources & evidence

ORD record
ord-07d7cd5d65b040748d7ef959fac048da
Source dataset
uspto-grants-2007_08
Patent number
US07259162B2

Reaction notes

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