Diisopropylethylamine → {1-[3-(5,6,7,8-Tetrahydro-[1,8]-naphthyridin-2-ylmethyl)-pyrrolidine-1-carbonyl]-piperidin-4-yl}-acetic acid ethyl ester

HRID 277888노트

반응식

HRID 277888 반응식
Cl.[NH:2]1[CH2:7][CH2:6][CH:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:4][CH2:3]1.CCN(C(C)C)C(C)C.ClC(Cl)(O[C:27](=[O:33])OC(Cl)(Cl)Cl)Cl.[N:35]1[C:44]2[NH:43][CH2:42][CH2:41][CH2:40][C:39]=2[CH:38]=[CH:37][C:36]=1[CH2:45][CH:46]1[CH2:50][CH2:49][NH:48][CH2:47]1>CC#N.CN(C=O)C>[CH2:12]([O:11][C:9](=[O:10])[CH2:8][CH:5]1[CH2:6][CH2:7][N:2]([C:27]([N:48]2[CH2:49][CH2:50][CH:46]([CH2:45][C:36]3[CH:37]=[CH:38][C:39]4[CH2:40][CH2:41][CH2:42][NH:43][C:44]=4[N:35]=3)[CH2:47]2)=[O:33])[CH2:3][CH2:4]1)[CH3:13]

참가 물질

7

반응물 4

HCID 81531Diisopropylethylamine2회HCID 94429TriphosgeneHCID 120171643-(5,6,7,8-Tetrahydro-[1,8]naphthyridin-2-ylmethyl)-pyrrolidineHCID 45358839Piperidin-4-yl-acetic acid ethyl ester hydrochloride

생성물 1

HCID 70160755{1-[3-(5,6,7,8-Tetrahydro-[1,8]-naphthyridin-2-ylmethyl)-pyrrolidine-1-carbonyl]-piperidin-4-yl}-acetic acid ethyl ester

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6342Acetonitrile용매2회

실험 절차

To a solution of 6-2 (31 mg, 0.15 mmol), DIPEA (77 μL, 0.44 mmol), and CH3CN (1.5 mL) at 0° C. was added dropwise a solution of triphosgene (15 mg, 52 mmol) in CH3CN (150 μL). Afer 30 min., a solution of 1-8 (43 mg, 0.15 mmol) and DIPEA (77 μL, 0.44 mmol) in DMF (0.8 mL) was added, followed by removal of the cooling bath. After 16 hrs, the reaction mixture was poured into EtOAc and sat. NaHCO3. The EtOAc portion was then washed with H2O and brine, dried (MgSO4), and concentrated. Flash chromatography (silica, 10% ethanol/EtOAc) gave 6-3 as a colorless oil.

후처리

  1. customfollowed by removal of the cooling bath
  2. additionthe reaction mixture was poured into EtOAc and sat. NaHCO3
  3. washThe EtOAc portion was then washed with H2O and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-8d616ea15c564bee8b112111b05b7320
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06358970B1

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