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Diisopropylethylamine → {(1S,2R)-2-[6-carbamoyl-5-(6-methyl-pyridin-2-ylamino)-pyridazin-3-ylamino]-cyclohexyl}-carbamic acid tert-butyl ester

HRID 1396358
ノート
印刷プレビュー

反応式

HRID 1396358 の反応式
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]=[CH:16][CH:15]=[C:14]([CH3:18])[N:13]=2)[CH:3]=1.C(N(CC)C(C)C)(C)C.[NH2:28][C@@H:29]1[CH2:34][CH2:33][CH2:32][CH2:31][C@@H:30]1[NH:35][C:36](=[O:42])[O:37][C:38]([CH3:41])([CH3:40])[CH3:39]>CN1CCCC1=O>[C:38]([O:37][C:36](=[O:42])[NH:35][C@H:30]1[CH2:31][CH2:32][CH2:33][CH2:34][C@H:29]1[NH:28][C:2]1[N:7]=[N:6][C:5]([C:8](=[O:9])[NH2:10])=[C:4]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[N:13]=2)[CH:3]=1)([CH3:41])([CH3:39])[CH3:40]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 1514389(1S,2R)-Cyclohexane-1,2-diamine, N1-BOC protectedHCID 866897076-Chloro-4-(6-methyl-pyridin-2-ylamino)-pyridazine-3-carboxylic acid amide

生成物 1

HCID 86689725{(1S,2R)-2-[6-carbamoyl-5-(6-methyl-pyridin-2-ylamino)-pyridazin-3-ylamino]-cyclohexyl}-carbamic acid tert-butyl ester収率 36.1%

試薬・触媒・溶媒 1

HCID 13387
N-methyl-2-pyrrolidone
溶媒

反応条件

温度
150 °C

実験手順

6-Chloro-4-(6-methyl-pyridin-2-ylamino)-pyridazine-3-carboxylic acid amide (130 mg, 0.49 mmol), N,N-diisopropylethylamine (0.17 mL, 0.986 mmol) and tert-butyl (1S,2R)-2-aminocyclohexylcarbamate (211 mg, 0.986 mmol) were dissolved in N-methylpyrrolidinone (2 mL) and heated at 150° C. for 2 d. The reaction mixture was cooled and concentrated in vacuo, then diluted with water, and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried (sodium sulfate), filtered and concentrated in vacuo. Purification by chromatography (silica, 0 to 5% methanol in dichloromethane) gave {(1S,2R)-2-[6-carbamoyl-5-(6-methyl-pyridin-2-ylamino)-pyridazin-3-ylamino]-cyclohexyl}-carbamic acid tert-butyl ester (78 mg, 35%) as a light brown amorphous residue. LCMS (EI/CI) m/z: 442 [M+H].

後処理

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated in vacuo
  3. additiondiluted with water
  4. extractionextracted with ethyl acetate
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried (sodium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customPurification by chromatography (silica, 0 to 5% methanol in dichloromethane)

出典と根拠

ORDレコード
ord-9aef6cd0c0ca4baa8f93d41293f5fd3c
出典データセット
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08901124B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート