Sulfuric acid magnesium salt (1:1) → (tert-butoxy)-N-(2-{[(2-chloro(1,3-thiazol-5-yl))methyl][(4-methoxyphenyl)methyl]amino}ethyl)carboxamide

HRID 1010543

反応式

HRID 1010543 の反応式
[Cl:1][C:2]1[S:3][C:4]([CH:7]=O)=[CH:5][N:6]=1.[C:9]([O:13][C:14]([NH:16][CH2:17][CH2:18][NH:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=1)=[O:15])([CH3:12])([CH3:11])[CH3:10].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].S([O-])([O-])(=O)=O.[Mg+2]>ClCCCl>[C:9]([O:13][C:14]([NH:16][CH2:17][CH2:18][N:19]([CH2:7][C:4]1[S:3][C:2]([Cl:1])=[N:6][CH:5]=1)[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=1)=[O:15])([CH3:12])([CH3:11])[CH3:10]

参加物

6

反応物 4

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 14797652-Chloro-1,3-thiazole-5-carbaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 112688707Tert-butyl N-(2-{[(4-methoxyphenyl)methyl]amino}ethyl)carbamate

生成物 1

HCID 131728996(tert-butoxy)-N-(2-{[(2-chloro(1,3-thiazol-5-yl))methyl][(4-methoxyphenyl)methyl]amino}ethyl)carboxamide収率 68.5%

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

実験手順

This compound was also made in a manner analogous to that set forth in Step D of Example 5, and Step A above, using 0.25 gram (0.0017 mole) of (2-chloro-1,3-thiazol-5-yl)formaldehyde, 0.47 gram (0.0017 mole) of (tert-butoxy)-N-(2-{[(4-methoxyphenyl)methyl]amino}ethyl)carboxamide, 0.54 gram (0.0025 mole) of sodium triacetoxyborohydride and 0.40 gram (0.0034 mole) of magnesium sulfate in about 10 mL of 1,2-dichloroethane. The reaction product was purified with column chromatography on silica gel. In a first chromatography, elution was accomplished using mixtures of 2% to 5% methanol in methylene chloride as eluants. In a second chromatography, elution was accomplished using a mixture of 1.5% methanol in methylene chloride as an eluant. Appropriate fractions were combined and concentrated under reduced pressure, yielding 0.48 gram of the subject compound. The NMR spectrum was consistent with the proposed structure.

後処理

  1. customThe reaction product was purified with column chromatography on silica gel
  2. washIn a first chromatography, elution
  3. washIn a second chromatography, elution
  4. additiona mixture of 1.5% methanol in methylene chloride as an eluant
  5. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-08bb04552a9841a980feb4305c89d2e8
出典データセット
uspto-grants-2011_07
特許番号
US07977332B2

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