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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
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HRID 1396359 반응식
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
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참가 물질

6

반응물 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

생성물 2

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

{(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].

후처리

  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

출처 및 근거

ORD 기록
ord-651c34a825aa4b988ecb21e775851081
출처 데이터셋
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08901124B2

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