2,4-Dichloro-1,3,5-triazine → tert-Butyl 5-(4-chloro-1,3,5-triazin-2-yl)hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate

HRID 244036

반응식

HRID 244036 반응식
Cl[C:2]1[N:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.[C:9]([O:13][C:14]([N:16]1[CH2:23][CH:22]2[CH:18]([CH2:19][NH:20][CH2:21]2)[CH2:17]1)=[O:15])([CH3:12])([CH3:11])[CH3:10].CCN(C(C)C)C(C)C>C(#N)C.[NH4+].[Cl-]>[Cl:8][C:6]1[N:5]=[CH:4][N:3]=[C:2]([N:20]2[CH2:19][CH:18]3[CH2:17][N:16]([C:14]([O:13][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:15])[CH2:23][CH:22]3[CH2:21]2)[N:7]=1

참가 물질

6

반응물 3

HCID 178102,4-Dichloro-1,3,5-triazineHCID 81531DiisopropylethylamineHCID 4142526Tert-butyl octahydropyrrolo(3,4-c)pyrrole-2-carboxylate

생성물 1

HCID 86669174tert-Butyl 5-(4-chloro-1,3,5-triazin-2-yl)hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate수율 44.1%

시약·촉매·용매 2

HCID 6342Acetonitrile용매2회HCID 25517Ammonium Chloride용매

실험 절차

To a solution of 2,4-dichloro-1,3,5-triazine (150 mg, 0.953 mmol) in ACN (5 mL) was added a solution of Intermediate 15 (202 mg, 0.953 mmol) and DIPEA (0.33 mL, 1.91 mmol) in ACN (5 mL) at 0° C. dropwise. After 10 min the mixture was diluted with saturated aqueous NH4Cl solution. The aqueous layer was then extracted with DCM and the combined organic extracts were dried over Na2SO4, filtered and concentrated in vacuo. Chromatography (Hexanes to 80% EtOAc/Hexanes) afforded the desired product as a white solid (137 mg, 44%). MS (ESI) mass calculated for C14H20ClN5O2, 325.13; m/z found, 326.1.

후처리

  1. extractionThe aqueous layer was then extracted with DCM
  2. dry with materialthe combined organic extracts were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-043734506eae4a778b5a28c884af9189
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08653263B2

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