1,2-Dichloroethane → 2-(4-{[(3,4-Dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-1,3-thiazole-5-carboxamide

HRID 2233926노트

반응식

HRID 2233926 반응식
C(N(C(C)C)CC)(C)C.C(Cl)CCl.C1C=NC2N(O)N=NC=2C=1.[Cl:24][C:25]1[C:29]([Cl:30])=[C:28]([CH3:31])[NH:27][C:26]=1[C:32]([NH:34][CH:35]1[CH2:40][CH2:39][N:38]([C:41]2C=CN=[C:43](S(C)=O)[N:42]=2)[CH2:37][CH2:36]1)=[O:33].Cl.NC1CCN(C2[S:59][C:60]([C:63]([NH2:65])=[O:64])=CN=2)CC1>CN(C=O)C>[Cl:24][C:25]1[C:29]([Cl:30])=[C:28]([CH3:31])[NH:27][C:26]=1[C:32]([NH:34][CH:35]1[CH2:36][CH2:37][N:38]([C:41]2[S:59][C:60]([C:63]([NH2:65])=[O:64])=[CH:43][N:42]=2)[CH2:39][CH2:40]1)=[O:33]

참가 물질

7

반응물 5

HCID 111,2-DichloroethaneHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 68579945HCID 68579945, 화합물2회HCID 68582668HCID 68582668, 화합물2회

생성물 1

HCID 685799292-(4-{[(3,4-Dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-1,3-thiazole-5-carboxamide수율 24.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Diisopropylethylamine (0.19 ml, 1.12 mmol), EDC (0.098 g, 0.51 mmol) and HOAT (0.070 g, 0.51 mmol) were added to a stirred solution of 3,4-dichloro-5-methyl-1H-pyrrole-2-carboxylic acid (Intermediate 3, 0.1 g, 0.51 mmol) in DMF (1.5 ml) at room temperature. The resultant solution was stirred for 30 mins and 2-(4-aminopiperidin-1-yl)-1,3-thiazole-5-carboxamide hydrochloride (Intermediate 81; 0.163 g, 0.62 mmol) was added. The reaction was stirred at room temperature overnight under nitrogen. The reaction was stirred overnight, then concentrated under vacuum and the residue was partitioned between water and EtOAc. The aqueous layer was extracted with EtOAc and the combined organic extracts were washed with 1 N HCl, water and brine, dried over MgSO4 and concentrated under vacuum. The residue was purified by reverse phase chromatography (water/acetonitrile gradient, 20-95%) to give the desired product as a white solid (50 mg).

후처리

  1. stirringThe reaction was stirred overnight
  2. concentrationconcentrated under vacuum
  3. customthe residue was partitioned between water and EtOAc
  4. extractionThe aqueous layer was extracted with EtOAc
  5. washthe combined organic extracts were washed with 1 N HCl, water and brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated under vacuum
  8. customThe residue was purified by reverse phase chromatography (water/acetonitrile gradient, 20-95%)

출처 및 근거

ORD 기록
ord-3757b77bba1f4c02a55bc45c14e36d2d
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07709503B2

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