4-(4-chlorophenoxy)Benzeneethanamine → HCID 178518123, 화합물

HRID 474875노트

반응식

HRID 474875 반응식
CS[C:3]1[NH:4][CH:5]=[C:6]([CH2:10][C:11]2[CH:12]=[N:13][CH:14]=[N:15][CH:16]=2)[C:7](=[O:9])[N:8]=1.[Cl:17][C:18]1[CH:33]=[CH:32][C:21]([O:22][C:23]2[CH:28]=[CH:27][C:26]([CH2:29][CH2:30][NH2:31])=[CH:25][CH:24]=2)=[CH:20][CH:19]=1>C(O)C>[Cl:17][C:18]1[CH:33]=[CH:32][C:21]([O:22][C:23]2[CH:28]=[CH:27][C:26]([CH2:29][CH2:30][NH:31][C:3]3[NH:4][CH:5]=[C:6]([CH2:10][C:11]4[CH:12]=[N:13][CH:14]=[N:15][CH:16]=4)[C:7](=[O:9])[N:8]=3)=[CH:25][CH:24]=2)=[CH:20][CH:19]=1

참가 물질

4

반응물 2

HCID 231324504-(4-chlorophenoxy)BenzeneethanamineHCID 178503543HCID 178503543, 화합물

생성물 1

HCID 178518123HCID 178518123, 화합물수율 60.2%

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
130 °C

실험 절차

2-Methylsulfanyl-5-pyrimidin-5-ylmethyl-1H-pyrimidin-4-one (30 mg, 0.128 mmol, 1 eq) and 2-[4-(4-Chloro-phenoxy)-phenyl]-ethylamine (47.5 mg, 0.192 mmol, 1.5 eq) were dissolved in dry ethanol (300 μl) and stirred at 130° C. for overnight. Reaction mixture was evaporated and crude residue was purified via Biotage SP-1 Snap Si 10 g; 15 ml/min; UV Wavelength (Collection: 254 nm; Monitor: 290 nm) in the gradient of MeOH in DCM: 0% for 1 CV, 0-8% for 15 CV. The appropriate fractions were combined and product was triturated with cyclohexane to give 2-{2-[4-(4-Chloro-phenoxy)-phenyl]-ethylamino}-5-pyrimidin-5-ylmethyl-1H-pyrimidin-4-one (0.077 mmol; yield: 60.2%, HPLC-MS/UV: [M+H]+=434.90; rt: 10.52 min; purity: 95%). 1H NMR (300 MHz; DMSO-d6) δ/ppm 2.77 (t, J=7.12 Hz, 2H), 3.40-3.50 (m, 2H), 3.52 (s, 2H), 6.34 (br.s., 1H), 6.90-7.03 (m, 4H), 7.25 (d, J=7.63, 2H), 7.40 (d, J=8.65, 2H), 7.68 (s, 1H), 8.66 (s, 2H), 8.97 (s, 1H), 10.85 (br.s., 1H)

후처리

  1. customReaction mixture
  2. customwas evaporated
  3. customcrude residue was purified via Biotage SP-1 Snap Si 10 g
  4. customUV Wavelength (Collection: 254 nm; Monitor: 290 nm) in the gradient of MeOH in DCM
  5. customproduct was triturated with cyclohexane

출처 및 근거

ORD 기록
ord-067420db60d04eab8785f8ce64870801
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08637536B2

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