Hydrochloric Acid → HCID 86667427, 화합물

HRID 74975노트

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HRID 74975 반응식
[NH2:1][CH2:2][C@:3]1([OH:18])[CH2:8][CH2:7][CH2:6][C@H:5]([NH:9][C:10]2[C:15]([F:16])=[CH:14][N:13]=[C:12]([Cl:17])[N:11]=2)[CH2:4]1.CCN(C(C)C)C(C)C.[C:28](Cl)(=[O:30])[CH3:29].Cl.[OH-].[Na+]>ClCCl>[Cl:17][C:12]1[N:11]=[C:10]([NH:9][C@H:5]2[CH2:6][CH2:7][CH2:8][C@:3]([CH2:2][NH:1][C:28](=[O:30])[CH3:29])([OH:18])[CH2:4]2)[C:15]([F:16])=[CH:14][N:13]=1

참가 물질

7

반응물 5

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 14798Sodium HydroxideHCID 81531DiisopropylethylamineHCID 86667425(1S,3S)-1-(aminomethyl)-3-(2-chloro-5-fluoropyrimidin-4-ylamino)cyclohexanol2회

생성물 1

HCID 86667427HCID 86667427, 화합물

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

(1S,3S)-1-(aminomethyl)-3-(2-chloro-5-fluoropyrimidin-4-ylamino)cyclohexanol, 46b, (0.19 g, 0.69 mmol) was dissolved in dichloromethane (15 mL) and treated with DIPEA (1.20 mL, 6.91 mmol) and acetyl chloride (0.10 mL, 1.38 mmol). After 5 minutes, the reaction mixture was diluted into 1N HCl (30 mL), and the aqueous layer was brought to a basic pH by addition of 1N NaOH. The resulting suspension was extracted with dichloromethane (50 mL). The organic layer was dried on Na2SO4 and concentrated in vacuo to provide the crude product, which was purified by silica gel chromatography (20-100% EtOAc/hexanes gradient) to afford 195 mg of N-{[(1S,3S)-3-(2-chloro-5-fluoropyrimidin-4-ylamino)-1-hydroxycyclo-hexyl]methyl}acetamide as a white foamy solid. LCMS RT=2.82 (M+1) 317.33.

후처리

  1. extractionThe resulting suspension was extracted with dichloromethane (50 mL)
  2. customThe organic layer was dried on Na2SO4
  3. concentrationconcentrated in vacuo
  4. customto provide the crude product, which
  5. customwas purified by silica gel chromatography (20-100% EtOAc/hexanes gradient)

출처 및 근거

ORD 기록
ord-341a0b7f201b4c90a78a2a62ad77b9be
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829007B2

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