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Trifluoroacetic acid → 6-((1R,2S)-2-amino-cyclohexylamino)-4-(6-methyl-pyridin-2-ylamino)-pyridazine-3-carboxylic acid amide

HRID 1396359
ノート
印刷プレビュー

反応式

HRID 1396359 の反応式
C([O:5]C(=O)[NH:7][C@H:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C@H:9]1[NH:14][C:15]1[N:16]=[N:17][C:18]([C:29](=[O:31])[NH2:30])=[C:19]([NH:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([CH3:28])[N:23]=2)[CH:20]=1)(C)(C)C.FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+]>ClCCl>[NH4+:7].[OH-:5].[NH2:7][C@H:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C@H:9]1[NH:14][C:15]1[N:16]=[N:17][C:18]([C:29]([NH2:30])=[O:31])=[C:19]([NH:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([CH3:28])[N:23]=2)[CH:20]=1
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

6

反応物 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 86689725{(1S,2R)-2-[6-carbamoyl-5-(6-methyl-pyridin-2-ylamino)-pyridazin-3-ylamino]-cyclohexyl}-carbamic acid tert-butyl ester

生成物 2

HCID 14923Ammonium HydroxideHCID 716267556-((1R,2S)-2-amino-cyclohexylamino)-4-(6-methyl-pyridin-2-ylamino)-pyridazine-3-carboxylic acid amide収率 83.9%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

{(1S,2R)-2-[6-Carbamoyl-5-(6-methyl-pyridin-2-ylamino)-pyridazin-3-ylamino]-cyclohexyl}-carbamic acid tert-butyl ester (188 mg, 0.426 mmol) was dissolved in dichloromethane (4 mL) then cooled to 0° C. Trifluoroacetic acid (2 mL, 25 mmol) was added drop-wise then the reaction mixture was warmed to 25° C. After 4 h, the mixture was cooled in an ice bath and neutralized with sodium bicarbonate solution. The mixture was extracted with ethyl acetate, and the combined organic layers washed with brine, dried (sodium sulfate), filtered, and concentrated in vacuo. Purification by chromatography (silica, 0 to 100% of a 0.1:0.01 solution of methanol:NH4OH in dichloromethane) gave 6-((1R,2S)-2-amino-cyclohexylamino)-4-(6-methyl-pyridin-2-ylamino)-pyridazine-3-carboxylic acid amide (61 mg, 42%) as a light brown solid. 1H NMR (400 MHz, DMSO-d6) d ppm 11.61 (s, 1H) 8.35-8.44 (m, 1H) 8.10 (s, 1H) 7.61 (br. s, 1H) 7.61 (t, J=7.3 Hz, 1H) 6.81-6.89 (m, 1H) 6.85 (d, J=7.3 Hz, 1H) 6.76 (d, J=8.1 Hz, 1H) 3.76-3.99 (m, 2H) 3.11-3.18 (m, 1H) 2.48-2.49 (m, 3H) 1.49-1.77 (m, 7H) 1.27-1.38 (m, 2H); LCMS (EI/CI) m/z: 342 [M+H].

後処理

  1. temperaturethe reaction mixture was warmed to 25° C
  2. temperaturethe mixture was cooled in an ice bath
  3. extractionThe mixture was extracted with ethyl acetate
  4. washthe combined organic layers washed with brine
  5. dry with materialdried (sodium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification by chromatography (silica, 0 to 100% of a 0.1:0.01 solution of methanol

出典と根拠

ORDレコード
ord-651c34a825aa4b988ecb21e775851081
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

読み込み中…

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