Triethylamine → HCID 71269539, compound

HRID 1429391Notes

Reaction equation

HRID 1429391 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]([OH:29])=O)(=[O:13])=[O:12])[CH:4]=[CH:3][CH:2]=1.[C:30]([NH:33][NH2:34])(=[O:32])[CH3:31].C(N(CC)CC)C>O=S(Cl)Cl.C(Cl)Cl.O>[C:30]([NH:33][NH:34][C:27](=[O:29])[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:13])=[O:12])[CH2:21][C:20]2[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=2[CH2:18][O:17][CH2:16]1)(=[O:32])[CH3:31]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 14039AcetohydrazideHCID 71269312HCID 71269312, compound

Product 1

HCID 71269539HCID 71269539, compoundYield 85.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 24386Thionyl ChlorideSolvent

Procedure

A solution of compound 21a (412 mg, 1 mmol) in SOCl2 (3 mL) was stirred for 1 h at rt and concentrated. Acetohydrazide (148 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 and concentrated. The crude product was purified by CC to give the compound 27a (400 mg, 85% yield).

Workup

  1. concentrationconcentrated
  2. extractionextracted with DCM (30 mL)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. concentrationconcentrated
  5. customThe crude product was purified by CC

Sources & evidence

ORD record
ord-17e801f3ffcf4fcba08e91617469e3db
Source dataset
uspto-grants-2015_01
Patent number
US08940722B2

Reaction notes

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