Diisopropylethylamine → HCID 57657406, compound

HRID 1920765Notes

Reaction equation

HRID 1920765 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]([C:21](=[O:24])[CH2:22]Cl)[C@@H:5]([CH2:14][CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)[C:6]([NH:8][C:9]1[S:10][CH:11]=[CH:12][N:13]=1)=[O:7].CCN(C(C)C)C(C)C>CN(C=O)C.O>[CH:15]1([CH2:14][C@H:5]([N:4]2[CH2:3][CH2:2][NH:1][CH2:22][C:21]2=[O:24])[C:6]([NH:8][C:9]2[S:10][CH:11]=[CH:12][N:13]=2)=[O:7])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

5

Reactant 2

HCID 81531DiisopropylethylamineHCID 57657416HCID 57657416, compound

Product 1

HCID 57657406HCID 57657406, compoundYield 90.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of compound 12E (1.12 g, 2.5 mmol) and DIEA (1.4 ml, 8 mmol) in DMF (15 ml) was maintained at ambient temperature for 30 minutes. Reaction mixture was diluted with water (150 ml) and extracted with EtOAc (2×150 ml). Organic layer was washed with 5% aq. sodium bicarbonate (100 ml) and brine (100 ml), dried over anh. MgSO4 and evaporated in vacuum to provide target product (758 mg, 90%) as light yellow oil. LC-MS [M+H] 337.2 (C16H24N4O2S+H, requires 337.46).

Workup

  1. customReaction mixture
  2. extractionextracted with EtOAc (2×150 ml)
  3. washOrganic layer was washed with 5% aq. sodium bicarbonate (100 ml) and brine (100 ml)
  4. dry with materialdried over anh. MgSO4
  5. customevaporated in vacuum

Sources & evidence

ORD record
ord-8166a5f72c6747238e8b4429e2249ef3
Source dataset
uspto-grants-2012_05
Patent number
US08173645B2

Reaction notes

Loading…