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Hydrochloric Acid → 5-(6-Bromo-2-phenyl-imidazo[1,2-a]pyridin-7-ylcarbamoyl)-1-methyl-1H-pyrazole-4-carboxylic acid

HRID 2382741
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HRID 2382741 반응식
[OH-].[Na+].C([O:5][C:6]([C:8]1[CH:9]=[N:10][N:11]([CH3:32])[C:12]=1[C:13](=[O:31])[NH:14][C:15]1[C:20]([Br:21])=[CH:19][N:18]2[CH:22]=[C:23]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[N:24]=[C:17]2[CH:16]=1)=[O:7])C.O.Cl>C1COCC1.CO>[Br:21][C:20]1[C:15]([NH:14][C:13]([C:12]2[N:11]([CH3:32])[N:10]=[CH:9][C:8]=2[C:6]([OH:7])=[O:5])=[O:31])=[CH:16][C:17]2[N:18]([CH:22]=[C:23]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[N:24]=2)[CH:19]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium Hydroxide2회HCID 670422785-(6-Bromo-2-phenyl-imidazo[1,2-a]pyridin-7-ylcarbamoyl)-1-methyl-1H-pyrazole-4-carboxylic acid ethyl ester

생성물 1

HCID 670416185-(6-Bromo-2-phenyl-imidazo[1,2-a]pyridin-7-ylcarbamoyl)-1-methyl-1H-pyrazole-4-carboxylic acid

시약·촉매·용매 2

HCID 887
Methanol
용매
HCID 8028Tetrahydrofuran용매

실험 절차

NaOH (3N, 0.65 ml) was added to a solution of 5-(6-bromo-2-phenyl-imidazo[1,2-a]pyridin-7-ylcarbamoyl)-1-methyl-1H-pyrazole-4-carboxylic acid ethyl ester (460 mg, 0.98 mmol) in a mixture of THF (5 ml) and methanol (5 ml), and the reaction mixture was stirred at r.t. overnight. An additional amount of NaOH (3N, 0.65 ml) and water (2 ml) were added and the mixture was heated to reflux (1 h). After cooling to r.t., HCl (conc., ˜0.7 ml) was added to the cooled mixture, and the brown suspension was stirred at r.t. (15 min). The suspension was then filtered, and the precipitated title compound (150 mg, 35%) was washed with a small amount of water, dried under vacuum, and used in the next step without further purification. MS (m/e)=440.3 [M+H+].

후처리

  1. temperaturethe mixture was heated
  2. temperatureto reflux (1 h)
  3. temperatureAfter cooling to r.t.
  4. stirringthe brown suspension was stirred at r.t. (15 min)
  5. filtrationThe suspension was then filtered
  6. customthe precipitated title compound (150 mg, 35%)
  7. washwas washed with a small amount of water
  8. customdried under vacuum
  9. customused in the next step without further purification

출처 및 근거

ORD 기록
ord-85dc7ca6634a4c189b8efd506f6fe397
출처 데이터셋
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08263584B2

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