HCID 1476965, 화합물 → HCID 57833087, 화합물

HRID 729640노트

반응식

HRID 729640 반응식
CN([CH:4]=[C:5]1[C:10](=O)[CH2:9][CH2:8][N:7]([CH3:12])[CH2:6]1)C.Cl.[NH2:14][C:15](=[NH:29])[N:16]1[CH2:20][CH2:19][C@@H:18]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:17]1.C[O-].[Na+]>CO>[C:24]([O:23][C:22](=[O:28])[NH:21][C@@H:18]1[CH2:19][CH2:20][N:16]([C:15]2[N:14]=[CH:4][C:5]3[CH2:6][N:7]([CH3:12])[CH2:8][CH2:9][C:10]=3[N:29]=2)[CH2:17]1)([CH3:26])([CH3:25])[CH3:27]

참가 물질

5

반응물 3

HCID 1476965HCID 1476965, 화합물HCID 10942334Sodium MethoxideHCID 86622701HCID 86622701, 화합물

생성물 1

HCID 57833087HCID 57833087, 화합물수율 58.3%

시약·촉매·용매 1

HCID 887Methanol용매2회

실험 절차

3-[(Dimethylamino)methylene]-1-methylpiperidin-4-one (9.04 g, 53.7 mmol) and tert-butyl {(3R)-1-[amino(imino)methyl]pyrrolidin-3-yl}carbamate hydrochloride (14.2 g, 53.7 mmol) were dissolved in methanol (100 mL) and to this was added dropwise sodium methoxide (9.66 g of a 30% solution in methanol). The reaction mixture was refluxed for 3 hours and then cooled to room temperature. The reaction mixture was then evaporated to dryness, and the residue was treated with water (50 mL). The precipitate was separated by filtration, washed with water (25 mL) and diethyl ether (50 mL) and dried to give the title compound 10.43 g (yield 58%). LCMS (ES+) M+H 334. 1H NMR (DMSO-d6) 1.39 (s, 9H) 1.85 (m, 1H) 2.13 (m, 1H) 2.33 (s, 3H) 2.60 (m, 2H) 2.67 (m, 2H) 3.23-3.26 (m, 1H) 3.31-3.37 (m, 3H) 3.40-3.536 (m, 1H) 3.63 (m, 1H) 4.04 (br s, 1H) 7.20 (br s, 1H) 8.04 (s, 1H).

후처리

  1. temperatureThe reaction mixture was refluxed for 3 hours
  2. customThe reaction mixture was then evaporated to dryness
  3. additionthe residue was treated with water (50 mL)
  4. customThe precipitate was separated by filtration
  5. washwashed with water (25 mL) and diethyl ether (50 mL)
  6. customdried

출처 및 근거

ORD 기록
ord-a379dd958560455bb00541f01fa20352
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07582643B2

반응 노트

불러오는 중…