Acetic Acid → HCID 22566248, 화합물

HRID 25170노트

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HRID 25170 반응식
[C:1]([C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][C:9]=1[F:10])[NH2:6])#[N:2].[N:11]([O-])=O.[Na+].C(O)(=O)C.[Br:19][C:20]1[CH:25]=[CH:24][C:23]([N:26]2[CH2:31][CH2:30][C:29]([C:32](=O)[CH3:33])=[C:28](O)[C:27]2=[O:36])=[CH:22][CH:21]=1>Cl.O.CO>[C:1]([C:3]1[CH:4]=[C:5]([N:6]2[C:28]3[C:27](=[O:36])[N:26]([C:23]4[CH:24]=[CH:25][C:20]([Br:19])=[CH:21][CH:22]=4)[CH2:31][CH2:30][C:29]=3[C:32]([CH3:33])=[N:11]2)[CH:7]=[CH:8][C:9]=1[F:10])#[N:2]

참가 물질

8

반응물 4

HCID 176Acetic AcidHCID 27376735-Amino-2-fluorobenzonitrileHCID 22566243HCID 22566243, 화합물HCID 23668193Sodium Nitrite

생성물 1

HCID 22566248HCID 22566248, 화합물

시약·촉매·용매 3

HCID 313Hydrochloric Acid용매2회HCID 887Methanol용매2회HCID 962Water용매2회

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온도
0 °C

실험 절차

3-Cyano-4-fluoroaniline (3.7 mmol, 0.5 g) in conc. HCl (4 mL) was cooled to 0° C. and NaNO2 (4.4 mmol, 0.3 g) in water (3 mL). This was stirred at 0° C. for 30 min, then acetic acid (1.3 mL) was added. SnCl2·(H2O)2 (8.5 mmol, 1.9 g) in 1:1 water:conc. HCl (3 mL) was added dropwise to the cold solution and stirred for an additional 30 min. To this mixture 1-[4-bromophenyl]-3-hydroxy-4-acetyl-5,6-dihydropyridin-2-one (3.9 mmol, 1.2 g) was slurried in MeOH (20 mL) and added with the aid of additional MeOH (6 mL). The suspension was heated at 50° C. for 3 h, then cooled at 10° C. for 18 h. The product, 1-[3-cyano-4-fluorophenyl]-3-methyl-6-[4-bromophenyl]-1,4,5,6-tetrahydro-7H-pyrazolo[3,4-c]pyridin-7-one, was isolated by filtration. There was obtained 1.34 g (3.2 mmol) of product; mp 237.6° C., LRMS (M+H)+: 425.2/427.1 m/z.

후처리

  1. stirringstirred for an additional 30 min
  2. temperatureThe suspension was heated at 50° C. for 3 h
  3. temperaturecooled at 10° C. for 18 h

출처 및 근거

ORD 기록
ord-12a5c411a99d44ab854390aad4e69c82
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06858616B2

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