1-Butanol → {[2-(6-Butoxy-pyridin-3-yl)-7-hydroxy-thiazolo[4,5-c]pyridine-6-carbonyl]-amino}-acetic acid methyl ester

HRID 642396노트

반응식

HRID 642396 반응식
C(O[C:4]([C:6]1[N:11]=[CH:10][C:9]2[N:12]=[C:13]([C:15]3[CH:16]=[N:17][C:18](Cl)=[CH:19][CH:20]=3)[S:14][C:8]=2[C:7]=1[OH:22])=[O:5])C.[CH3:23][CH2:24][CH2:25][CH2:26][O-:27].[Na+].C(O)CCC.Cl.CN(C)CCCN=C=NCC.Cl.[CH3:47][O:48][C:49](=[O:52])[CH2:50][NH2:51].Cl>CN(C)C1C=CN=CC=1.CN(C)C=O.C(Cl)(Cl)Cl>[CH3:47][O:48][C:49](=[O:52])[CH2:50][NH:51][C:4]([C:6]1[N:11]=[CH:10][C:9]2[N:12]=[C:13]([C:15]3[CH:16]=[N:17][C:18]([O:27][CH2:26][CH2:25][CH2:24][CH3:23])=[CH:19][CH:20]=3)[S:14][C:8]=2[C:7]=1[OH:22])=[O:5]

참가 물질

10

반응물 6

HCID 2631-ButanolHCID 313Hydrochloric AcidHCID 122755Glycine methyl ester hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 23669364Sodium n-butylateHCID 866173622-(6-Chloro-pyridin-3-yl)-7-hydroxy-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester

생성물 1

HCID 68428062{[2-(6-Butoxy-pyridin-3-yl)-7-hydroxy-thiazolo[4,5-c]pyridine-6-carbonyl]-amino}-acetic acid methyl ester

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 6212Chloroform용매HCID 6228Dimethylformamide용매

실험 절차

2-(6-Chloro-pyridin-3-yl)-7-hydroxy-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester, example 92(c)(0.15 g, 0.45 mmol) was added to a solution of sodium 1-butoxide in 1-butanol (prepared by dissolving sodium (45.2 mg, 1.96 mmol) in 10 mL of anhydrous 1-butanol) at ambient temperature. After the reaction mixture was refluxed overnight, the solvent was evaporated off. The resulting residue was added to a suspension of N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (94.3 mg, 0.49 mmol), glycine methyl ester hydrochloride (61.8 mg, 0.49 mmol), hydrochloric acid (10 N, 98.3 μL, 0.983 mmol), and 4-dimethylaminopyridine (5.46 mg, 0.045 mmol) in N,N-dimethylformamide at ambient temperature. The reaction mixture was stirred at ambient temperature overnight before 60 mL of chloroform was added. The organic solution was washed with saturated ammonium chloride solution, brine, saturated sodium bicarbonate solution, and brine, dried, filtered, and concentrated. The crude product was purified by flash chromatography eluting from silica gel with a gradient of 0-100% ethyl acetate in hexanes to produce 10.6 mg of a white solid. MS: (+) m/z 417.3 (M+1).

후처리

  1. temperatureAfter the reaction mixture was refluxed overnight
  2. customthe solvent was evaporated off
  3. additionwas added
  4. washThe organic solution was washed with saturated ammonium chloride solution, brine, saturated sodium bicarbonate solution, and brine
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by flash chromatography
  9. washeluting from silica gel with a gradient of 0-100% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-a23acd0a0ca74b919272be4243b13ce2
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07696223B2

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