Dimethylamine → HCID 71269506, compound

HRID 1429390Notes

Reaction equation

HRID 1429390 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.[CH3:30][NH:31][CH3:32].C(N(CC)CC)C>O=S(Cl)Cl.C(Cl)Cl.O>[CH3:30][N:31]([CH3:32])[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: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 3

HCID 674DimethylamineHCID 8471TriethylamineHCID 71269312HCID 71269312, compound

Product 1

HCID 71269506HCID 71269506, compoundYield 38%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 24386Thionyl ChlorideSolvent

Procedure

A solution of compound 21a (100 mg, 0.24 mmol) in SOCl2 (3 mL) was stirred at rt for 1 h and concentrated. Dimethylamine (32.8 mg, 0.4 mmol) and triethylamine (81 mg, 0.81 mmol) in DCM (5 mL) were added to the above residue. The mixture was stirred at rt for 1 h. The mixture was taken up in H2O (10 mL) and extracted with DCM (30 mL). The organic layers were dried over Na2SO4 and concentrated. The crude product was purified Prep-TLC to give the pure compound 26 (40 mg, 38% yield). LCMS (m/z): 440.1 (MH+).

Workup

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

Sources & evidence

ORD record
ord-977c41834a5c434a8e10f3b2783f216f
Source dataset
uspto-grants-2015_01
Patent number
US08940722B2

Reaction notes

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