Dichloromethane → HCID 57982545, compound

HRID 1868481Notes

Reaction equation

HRID 1868481 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]3[CH:14]=[C:15]([S:17](Cl)(=[O:19])=[O:18])[N:16]=[C:12]3[N:11]=[C:10]([CH3:21])[C:9]=2[C:22]#[N:23])=[C:4](C)[CH:3]=1.[NH:25]1[CH2:29][CH2:28][C@H:27]([NH:30][C:31](=[O:33])[CH3:32])[CH2:26]1.CCN(CC)CC.C(Cl)[Cl:42]>>[C:22]([C:9]1[C:10]([CH3:21])=[N:11][C:12]2[N:13]([CH:14]=[C:15]([S:17]([N:25]3[CH2:29][CH2:28][C@H:27]([NH:30][C:31](=[O:33])[CH3:32])[CH2:26]3)(=[O:19])=[O:18])[N:16]=2)[C:8]=1[C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][C:4]=1[Cl:42])#[N:23]

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 7021471(S)-(-)-3-AcetamidopyrrolidineHCID 57982501HCID 57982501, compound

Product 1

HCID 57982545HCID 57982545, compoundYield 81%

Procedure

To a stirred solution of 5-(4-chloro-2-methylphenyl)-6-cyano-7-methylimidazo[1,2-a]pyrimidine-2-sulfonyl chloride (34 mg, 0.09 mmol) in CH2Cl2 (2 mL) was added (S)—N-(pyrrolidin-3-yl) acetamide (16.3 mg, 0.13 mol) and Et3N (20 mg, 0.2 mmol). After 14 h, the reaction was extracted with 1N HCl (2 mL×2) before drying over MgSO4. Filtration and concentration under reduced pressure afforded (S)—N-(1-(6-cyano-5-(2,4-dichlorophenyl)-7-methylimidazo[1,2-a]pyrimidin-2-ylsulfonyl)pyrrolidin-3-yl)acetamide as a white solid (34 mg, 81%). This crude product was used directly for the subsequent reaction without further purification.

Workup

  1. extractionthe reaction was extracted with 1N HCl (2 mL×2)
  2. dry with materialbefore drying over MgSO4
  3. filtrationFiltration and concentration under reduced pressure

Sources & evidence

ORD record
ord-8d24a1742e124106b549141bfd70eafe
Source dataset
uspto-grants-2009_12
Patent number
US07635699B2

Reaction notes

Loading…