2-Fluoroethanol → HCID 178424913, 화합물

HRID 80852

반응식

HRID 80852 반응식
Cl[C:2]1[C:3]2[CH2:24][N:23]([C:25]3[CH:30]=[C:29]([CH:31]([CH3:33])[CH3:32])[CH:28]=[CH:27][C:26]=3[CH3:34])[CH2:22][CH2:21][C:4]=2[N:5]=[C:6]([C:8]2[C:16]([CH3:17])=[CH:15][CH:14]=[C:13]3[C:9]=2[C:10]([CH3:20])=[N:11][N:12]3C=O)[N:7]=1.[F:35][CH2:36][CH2:37][OH:38].[H-].[Na+]>C1COCC1>[CH3:20][C:10]1[C:9]2[C:13](=[CH:14][CH:15]=[C:16]([CH3:17])[C:8]=2[C:6]2[N:7]=[C:2]([O:38][CH2:37][CH2:36][F:35])[C:3]3[CH2:24][N:23]([C:25]4[CH:30]=[C:29]([CH:31]([CH3:32])[CH3:33])[CH:28]=[CH:27][C:26]=4[CH3:34])[CH2:22][CH2:21][C:4]=3[N:5]=2)[NH:12][N:11]=1

참가 물질

5

반응물 3

HCID 97372-FluoroethanolHCID 24758Sodium hydrideHCID 866902884-(4-chloro-6-(5-isopropyl-2-methylphenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-yl)-3,5-dimethyl-1H-indazole-1-carbaldehyde

생성물 1

HCID 178424913HCID 178424913, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 4-(4-chloro-6-(5-isopropyl-2-methylphenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-yl)-3,5-dimethyl-1H-indazole-1-carbaldehyde (30 mg, 0.063 mmol) in THF (3 mL) was added 2-fluoroethanol (16.2 mg, 0.25 mmol) and NaH (15.1 mg, 0.63 mmol, 60% in mineral oil). The mixture was stirred at room temperature for 4 h. LC-MS showed reaction complete. The reaction mixture was concentrated and the residue was partitioned between saturated aqueous NH4Cl solution and DCM. The layers were separated and the aqueous layer was extracted further with DCM. The organics were combined and concentrated. The residue was purified by FCC (0-100% EtOAc/heptane) to provide 2-(3,5-dimethyl-1H-indazol-4-yl)-4-(2-fluoroethoxy)-6-(5-isopropyl-2-methylphenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine. 1H NMR (400 MHz, METHANOL-d4) δ ppm 7.47 (d, J=8.59 Hz, 1H), 7.34 (s, 1H), 7.15 (d, J=7.71 Hz, 1H), 7.06 (d, J=1.39 Hz, 1H), 6.92 (dd, J=1.52, 7.71 Hz, 1H), 4.71-4.81 (m, 2H), 4.67 (s, 2H), 4.13 (s, 2H), 3.33-3.39 (m, 2H), 3.05 (t, J=5.56 Hz, 2H), 2.88 (td, J=6.93, 13.80 Hz, 1H), 2.32 (s, 3H), 2.27 (s, 3H), 1.98 (s, 3H), 1.25 (d, J=6.82 Hz, 6H); MS (ESE) m/z 474.4 (M+H)+.

후처리

  1. customreaction complete
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue was partitioned between saturated aqueous NH4Cl solution and DCM
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted further with DCM
  6. concentrationconcentrated
  7. customThe residue was purified by FCC (0-100% EtOAc/heptane)

출처 및 근거

ORD 기록
ord-04b0c18196cf48118e1f05072d283ab4
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846656B2

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