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

HRID 642396ノート

反応式

HRID 642396 の反応式
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]

参加物

10

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 6212Chloroform溶媒HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-a23acd0a0ca74b919272be4243b13ce2
出典データセット
uspto-grants-2010_04
特許番号
US07696223B2

反応ノート

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