Water → 5-chloro-N-[1,3-dioxo-2-(4-piperidinyl)-2,3-dihydro-1H-isoindol-4-yl]-2-thiophenecarboxamide

HRID 1455681노트

반응식

HRID 1455681 반응식
C(O)(C(F)(F)F)=O.O.[Cl:9][C:10]1[S:14][C:13]([C:15]([NH:17][C:18]2[CH:26]=[CH:25][CH:24]=[C:23]3[C:19]=2[C:20](=[O:41])[N:21]([CH:28]2[CH2:33][CH2:32][N:31](C(OC(C)(C)C)=O)[CH2:30][CH2:29]2)[C:22]3=[O:27])=[O:16])=[CH:12][CH:11]=1>C(Cl)(Cl)Cl>[Cl:9][C:10]1[S:14][C:13]([C:15]([NH:17][C:18]2[CH:26]=[CH:25][CH:24]=[C:23]3[C:19]=2[C:20](=[O:41])[N:21]([CH:28]2[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)[C:22]3=[O:27])=[O:16])=[CH:12][CH:11]=1

참가 물질

5

반응물 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 18440735tert-Butyl 4-(4-{[(5-chloro-2-thienyl)carbonyl]amino}-1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)tetrahydro-1(2H)-pyridinecarboxylate

생성물 1

HCID 120748935-chloro-N-[1,3-dioxo-2-(4-piperidinyl)-2,3-dihydro-1H-isoindol-4-yl]-2-thiophenecarboxamide

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

50 ml of a mixture of TFA and water (9:1) are added dropwise to an ice-cooled mixture of 1.82 g (3.71 mmol) of tert-butyl 4-(4-{[(5-chloro-2-thienyl)carbonyl]-amino}-1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)tetrahydro-1(2H)-pyridine-carboxylate in 50 ml of chloroform. The ice-cooling is removed and the mixture is stirred at room temperature for 1.5 h and then concentrated. The residue is taken up in dichloromethane/methanol and washed with sat. sodium bicarbonate solution, dried over magnesium sulfate and concentrated. The crude product can be purified further by crystallization with ether. Yield: 1.185 g (78% of theory); MS (DCI, NH4): m/z (%)=390 (M+H, 100).

후처리

  1. temperaturecooled
  2. customis removed
  3. concentrationconcentrated
  4. washwashed with sat. sodium bicarbonate solution
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe crude product can be purified further by crystallization with ether

출처 및 근거

ORD 기록
ord-d188d57c8ea34dc2adff32540031c438
출처 데이터셋
uspto-grants-2009_01
특허 번호
US07482472B2

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