Einecs 211-027-4 → HCID 178519562、化合物

HRID 2177606ノート

反応式

HRID 2177606 の反応式
[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]

参加物

3

反応物 2

HCID 69401Einecs 211-027-4HCID 90409201HCID 90409201、化合物

生成物 1

HCID 178519562HCID 178519562、化合物収率 19.3%

反応条件

温度
170 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-8b90ce0c940e44638177dfe2c96dc3ea
出典データセット
uspto-grants-2015_06
特許番号
US09066946B2

反応ノート

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