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Cesium carbonate → methyl 5-[(3-{[(1S)-1-(hydroxymethyl)propyl]oxy}-5-{[(1-methyl-1H-pyrazol-3-yl)amino]carbonyl}phenyl)oxy]pyrazine-2-carboxylate

HRID 1011751
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HRID 1011751 반응식
Cl[C:2]1[N:3]=[CH:4][C:5]([C:8]([O:10][CH3:11])=[O:9])=[N:6][CH:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[OH:18][C:19]1[CH:20]=[C:21]([CH:31]=[C:32]([O:34][C@H:35]([CH2:38][OH:39])[CH2:36][CH3:37])[CH:33]=1)[C:22]([NH:24][C:25]1[CH:29]=[CH:28][N:27]([CH3:30])[N:26]=1)=[O:23]>C(#N)C>[OH:39][CH2:38][C@@H:35]([O:34][C:32]1[CH:33]=[C:19]([O:18][C:2]2[N:3]=[CH:4][C:5]([C:8]([O:10][CH3:11])=[O:9])=[N:6][CH:7]=2)[CH:20]=[C:21]([C:22]([NH:24][C:25]2[CH:29]=[CH:28][N:27]([CH3:30])[N:26]=2)=[O:23])[CH:31]=1)[CH2:36][CH3:37]
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5

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HCID 10796Cesium carbonateHCID 406081Methyl 5-chloropyrazine-2-carboxylateHCID 591271493-hydroxy-5-{[(1S)-1-(hydroxymethyl)propyl]oxy}-N-(1-methyl-1H-pyrazol-3-yl)benzamide

생성물 1

HCID 59127088methyl 5-[(3-{[(1S)-1-(hydroxymethyl)propyl]oxy}-5-{[(1-methyl-1H-pyrazol-3-yl)amino]carbonyl}phenyl)oxy]pyrazine-2-carboxylate수율 16.3%

시약·촉매·용매 1

HCID 6342
Acetonitrile
용매

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온도
160 °C

실험 절차

Methyl 5-chloropyrazine-2-carboxylate (104 mg, 0.60 mmol) and cesium carbonate (467 mg, 1.43 mmol) were added to a solution of 3-hydroxy-5-{[(1S)-1-(hydroxymethyl)propyl]oxy}-N-(1-methyl-1H-pyrazol-3-yl)benzamide (175 mg, 0.570 mmol), in acetonitrile (5 mL) and the mixture heated in a microwave reactor at 160° C. for 330 minutes. The acetonitrile was removed in vacuo and the residue dissolved in ethyl acetate (25 mL), washed with water (20 mL), brine (20 mL), dried (MgSO4) and evaporated to a residue which was chromatographed by preparative HPLC on C18 reversed phase, eluting with 5-95% acetonitrile (+0.2% TFA) in water (+0.2% TFA), to give the required product (41 mg). 1H NMR δ (CDCl3): 0.97 (t, 3H), 1.78 (quin, 2H), 3.82 (s, 3H), 3.91 (s, 3H), 4.52 (m, 3H), 4.66 (quin, 1H), 6.59 (t, 1H), 6.89 (d, 1H), 7.05 (t, 1H), 7.15 (t, 1H), 8.19 (d, 1H), 8.79 (d, 1H), 9.86 (s, 1H); m/z 442 (M+H)+

후처리

  1. customThe acetonitrile was removed in vacuo
  2. dissolutionthe residue dissolved in ethyl acetate (25 mL)
  3. washwashed with water (20 mL), brine (20 mL)
  4. dry with materialdried (MgSO4)
  5. customevaporated to a residue which
  6. customwas chromatographed by preparative HPLC on C18 reversed phase
  7. washeluting with 5-95% acetonitrile (+0.2% TFA) in water (+0.2% TFA)

출처 및 근거

ORD 기록
ord-704bd8cac4db49e390e2ada796e84bdf
출처 데이터셋
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07977328B2

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