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Diisopropylethylamine → Tert-butyl 4-({1-[(6-methylpyridin-3-yl)carbonyl]azetidin-3-yl]carbonyl)-1,4-diazepane-1-carboxylate

HRID 1402755
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HRID 1402755 반응식
[NH:1]1[CH2:4][CH:3]([C:5]([N:7]2[CH2:13][CH2:12][CH2:11][N:10]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:9][CH2:8]2)=[O:6])[CH2:2]1.CCN(C(C)C)C(C)C.[CH3:30][C:31]1[N:36]=[CH:35][C:34]([C:37](Cl)=[O:38])=[CH:33][CH:32]=1>C(Cl)Cl>[CH3:30][C:31]1[N:36]=[CH:35][C:34]([C:37]([N:1]2[CH2:4][CH:3]([C:5]([N:7]3[CH2:13][CH2:12][CH2:11][N:10]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:9][CH2:8]3)=[O:6])[CH2:2]2)=[O:38])=[CH:33][CH:32]=1
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참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 218904586-Methylnicotinoyl chlorideHCID 66739652Tert-butyl 4-(azetidin-3-ylcarbonyl)-1,4-diazepane-1-carboxylate

생성물 1

HCID 66739625Tert-butyl 4-({1-[(6-methylpyridin-3-yl)carbonyl]azetidin-3-yl]carbonyl)-1,4-diazepane-1-carboxylate수율 36.4%

시약·촉매·용매 1

HCID 6344Dichloromethane
용매
3회

실험 절차

To a stirred solution of tert-butyl 4-(azetidin-3-ylcarbonyl)-1,4-diazepane-1-carboxylate (1.02 g, 3.6 mmol) and DIPEA (1.41 g, 10.8 mmol) in DCM (20 mL) was added a solution of 6-methylpyridine-3-carbonyl chloride (420 mg, 4.32 mmol) in DCM (5 mL) at 0° C. After 3 hours the reaction was diluted with DCM (10 mL), washed with saturated aqueous NaHCO3 (10 mL), brine (5 mL), dried (MgSO4), filtered and concentrated at reduced pressure. Purification by silica FCC (eluting with 100:0:0 to 95:4.5:0.5 gradient of DCM/MeOH/NH3) gave the title compound (527 mg, 36%) as an orange-brown oil.

후처리

  1. washwashed with saturated aqueous NaHCO3 (10 mL), brine (5 mL)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated at reduced pressure
  5. customPurification
  6. washby silica FCC (eluting with 100:0:0 to 95:4.5:0.5 gradient of DCM/MeOH/NH3)

출처 및 근거

ORD 기록
ord-0d8891ce1c9244c98d578357879f29ec
출처 데이터셋
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08912176B2

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