Hydrochloric Acid → HCID 57594555, 화합물

HRID 222880노트

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HRID 222880 반응식
[OH:1][CH2:2][CH2:3][C@@H:4]([NH:24][C:25](=[O:31])OC(C)(C)C)[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:13]=[C:14]3[C:19]([CH:20]([OH:22])[CH3:21])=[CH:18][CH:17]=[CH:16][N:15]3[CH:23]=2)=[CH:8][CH:7]=1.Cl.O1CCOCC1.C(N(CC)C(C)C)(C)C.[Cl:48][C:49]1[CH:50]=[C:51]([CH:66]=[CH:67][C:68]=1[O:69][CH:70]([CH3:72])[CH3:71])C(OC1C(F)=C(F)C(F)=C(F)C=1F)=O>O>[Cl:48][C:49]1[CH:50]=[C:51]([CH:66]=[CH:67][C:68]=1[O:69][CH:70]([CH3:72])[CH3:71])[C:25]([NH:24][C@@H:4]([CH2:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]2[N:13]=[C:14]3[C:19]([CH:20]([OH:22])[CH3:21])=[CH:18][CH:17]=[CH:16][N:15]3[CH:23]=2)=[CH:10][CH:11]=1)[CH2:3][CH2:2][OH:1])=[O:31]

참가 물질

7

반응물 5

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 81531DiisopropylethylamineHCID 57594128HCID 57594128, 화합물HCID 57594302HCID 57594302, 화합물

생성물 1

HCID 57594555HCID 57594555, 화합물수율 53%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A mixture of 1,1-dimethylethyl [(1S)-3-hydroxy-1-({4-[8-(1-hydroxyethyl)imidazo[1,2-a]pyridin-2-yl]phenyl}methyl)propyl]carbamate (1.08 g, 2.54 mmol) and 4M HCl in 1,4-dioxane (8.0 mL, 32 mmol) was stirred at room temperature for 30 minutes. The reaction was concentrated to dryness, redissolved in DMF (25 mL), and to this solution was added N,N-diisopropylethylamine (1.64 g, 12.7 mmol) and pentafluorophenyl 3-chloro-4[(1-methylethyl)oxy]benzoate (0.963 g, 2.54 mmol). The mixture was stirred for 3.0 h at room temperature, diluted with water, and extracted into ethyl acetate. The extracts were washed with water and saturated sodium chloride, dried (Na2SO4), and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (2% MeOH:EtOAc) to give the title compound (0.7 g, 53%) as a pale yellow powder. MS (ES+) m/e 522 [M+H]+.

후처리

  1. concentrationThe reaction was concentrated to dryness
  2. dissolutionredissolved in DMF (25 mL)
  3. stirringThe mixture was stirred for 3.0 h at room temperature
  4. extractionextracted into ethyl acetate
  5. washThe extracts were washed with water and saturated sodium chloride
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash chromatography on silica gel (2% MeOH:EtOAc)

출처 및 근거

ORD 기록
ord-e0dd4a5cdf354b27a2902474b2e76d24
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08207340B2

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