Einecs 211-027-4 → HCID 178519562, 화합물

HRID 2177606노트

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HRID 2177606 반응식
[Cl:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:5]=[CH:4][C:3]=1[C:12]([N:14]1[CH2:19][CH2:18][C:17]2=[C:20]([C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=3)[N:21](C)[N:22]=[C:16]2[CH2:15]1)=[O:13].[Cl-].[NH+]1C=CC=CC=1>>[Cl:1][C:2]1[C:7]([C:8]([F:11])([F:9])[F:10])=[CH:6][CH:5]=[CH:4][C:3]=1[C:12]([N:14]1[CH2:19][CH2:18][C:17]2=[C:20]([C:24]3[CH:25]=[CH:26][C:27]([F:30])=[CH:28][CH:29]=3)[NH:21][N:22]=[C:16]2[CH2:15]1)=[O:13]

참가 물질

3

반응물 2

HCID 69401Einecs 211-027-4HCID 90409201HCID 90409201, 화합물

생성물 1

HCID 178519562HCID 178519562, 화합물수율 19.3%

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온도
170 °C

실험 절차

To a vial containing 6-{[2-Chloro-3-(trifluoromethyl)phenyl]carbonyl}-3-(4-fluorophenyl)-2-methyl-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-c]pyridine (50 mg, 0.11 mmol) was added pyridinium chloride (270 mg, 2.30 mmol). The vial was flushed with N2 and heated to 170° C. for 30 min in a microwave reactor. To the reaction was added EtOAc and 1M NaOH. The layers were separated and the water layer was extracted with EtOAc three times. The combined organic layers were concentrated in vacuo and the residue was purified by HPLC (Gilson prep system, inertsil ODS-3, C18, 3 μm 30×100 mm column at 45° C., gradient of 5-70% MeCN/water with 0.05% TFA over 7 min, flow rate of 80 mL/min). The product was isolated as orange oil (9 mg, 19%) MS (ESI): mass calcd. for C20H14ClF4N3O, 423.8. m/z found, 424.2 [M+H]+. 1H NMR (500 MHz, CDCl3) δ 7.82-7.69 (m, 1H), 7.58-7.38 (m, 4H), 7.18-7.13 (m, 2H), 5.01 (m, 1H), 4.48-4.39 (m, 1H), 4.30-3.87 (m, 1H), 3.60-3.40 (m, 1H), 2.94 (t, J=5.8 Hz, 1H), 2.86-2.65 (m, 1H).

후처리

  1. customThe vial was flushed with N2
  2. additionTo the reaction was added EtOAc and 1M NaOH
  3. customThe layers were separated
  4. extractionthe water layer was extracted with EtOAc three times
  5. concentrationThe combined organic layers were concentrated in vacuo
  6. customthe residue was purified by HPLC (Gilson prep system, inertsil ODS-3, C18, 3 μm 30×100 mm column at 45° C., gradient of 5-70% MeCN/water with 0.05% TFA over 7 min, flow rate of 80 mL/min)

출처 및 근거

ORD 기록
ord-8b90ce0c940e44638177dfe2c96dc3ea
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09066946B2

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