Triethylamine → HCID 71269526, compound

HRID 1429393Notes

Reaction equation

HRID 1429393 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[S:11]([N:14]2[CH2:21][C:20]3[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=3[CH2:18][O:17][CH2:16][C@H:15]2[CH2:26][C:27](O)=[O:28])(=[O:13])=[O:12])[CH:4]=[CH:3][CH:2]=1.O=S(Cl)Cl.[NH2:34][CH2:35][C:36]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)=[O:37].C(N(CC)CC)C>C(Cl)Cl.O>[O:37]=[C:36]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[CH2:35][NH:34][C:27](=[O:28])[CH2:26][C@H:15]1[N:14]([S:11]([C:9]2[CH:8]=[CH:7][CH:6]=[C:5]3[C:10]=2[N:1]=[CH:2][CH:3]=[CH:4]3)(=[O:12])=[O:13])[CH2:21][C:20]2[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=2[CH2:18][O:17][CH2:16]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 11952PhenacylamineHCID 24386Thionyl ChlorideHCID 71269312HCID 71269312, compound

Product 1

HCID 71269526HCID 71269526, compoundYield 75.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of compound 21a (412 mg, 1 mmol) and SOCl2 (3 mL) was stirred at rt for 1 h and concentrated. 2-Amino-1-phenylethanone (342 mg, 2 mmol) and triethylamine (303 mg, 3 mmol) in DCM (5 mL) were added to the above residue. The mixture was stirred at rt for 1 h. The reaction was taken up in H2O (10 mL) and extracted with DCM (30 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated. The crude product was purified by CC to give compound 28a (400 mg, 75% yield).

Workup

  1. concentrationconcentrated
  2. stirringThe mixture was stirred at rt for 1 h
  3. extractionextracted with DCM (30 mL)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by CC

Sources & evidence

ORD record
ord-68caefc84b1d4ed0a8d9a922e7189bc7
Source dataset
uspto-grants-2015_01
Patent number
US08940722B2

Reaction notes

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