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(1S,2R)-Cyclohexane-1,2-diamine, N1-BOC protected → tert-butyl (1S,2R)-2-(6-carbamoyl-5-(4-methyl-6-propylpyridin-2-ylamino)pyridazin-3-ylamino)cyclohexylcarbamate

HRID 1396471
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HRID 1396471 반응식
Cl[C:2]1[N:7]=[N:6][C:5]([C:8]([NH2:10])=[O:9])=[C:4]([NH:11][C:12]2[CH:17]=[C:16]([CH3:18])[CH:15]=[C:14]([CH2:19][CH2:20][CH3:21])[N:13]=2)[CH:3]=1.[NH2:22][C@@H:23]1[CH2:28][CH2:27][CH2:26][CH2:25][C@@H:24]1[NH:29][C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33]>CN1C(=O)CCC1.C(OCC)(=O)C.[Cl-].[Na+].O>[C:8]([C:5]1[N:6]=[N:7][C:2]([NH:22][C@@H:23]2[CH2:28][CH2:27][CH2:26][CH2:25][C@@H:24]2[NH:29][C:30](=[O:36])[O:31][C:32]([CH3:34])([CH3:33])[CH3:35])=[CH:3][C:4]=1[NH:11][C:12]1[CH:17]=[C:16]([CH3:18])[CH:15]=[C:14]([CH2:19][CH2:20][CH3:21])[N:13]=1)(=[O:9])[NH2:10]
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참가 물질

6

반응물 2

HCID 1514389(1S,2R)-Cyclohexane-1,2-diamine, N1-BOC protectedHCID 86689801HCID 86689801, 화합물

생성물 1

HCID 86689802tert-butyl (1S,2R)-2-(6-carbamoyl-5-(4-methyl-6-propylpyridin-2-ylamino)pyridazin-3-ylamino)cyclohexylcarbamate수율 43%

시약·촉매·용매 3

HCID 8857Ethyl Acetate용매HCID 13387N-methyl-2-pyrrolidone
용매
HCID 57417360Sodium chloride; water용매

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온도
140 °C

실험 절차

To a solution of 6-chloro-4-(4-methyl-6-propylpyridin-2-ylamino)pyridazine-3-carboxamide (134 mg, 438 μmol) in NMP (1.5 mL) was added tert-butyl (1S,2R)-2-aminocyclohexylcarbamate (376 mg, 1.75 mmol) in 3 portions approximately every 12 h over 36 h, with heating at 140° C. in the periods between additions. The mixture was then diluted with ethyl acetate and brine. The phases were separated and the organic phase washed twice with brine. The organic phase was concentrated in vacuo and then purified by chromatography (silica, 30 to 100% ethyl acetate in hexanes) to give tert-butyl (1S,2R)-2-(6-carbamoyl-5-(4-methyl-6-propylpyridin-2-ylamino)pyridazin-3-ylamino)cyclohexylcarbamate (91 mg, 188 μmol, 43%) as a light brown solid. MS (EI/CI) m/z: 484.3 [M+H].

후처리

  1. customThe phases were separated
  2. washthe organic phase washed twice with brine
  3. concentrationThe organic phase was concentrated in vacuo
  4. custompurified by chromatography (silica, 30 to 100% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-bbdd78dab214401288725c23e95f38ee
출처 데이터셋
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08901124B2

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