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

Reaction equation

HRID 1010543 reaction equation
[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]

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-08bb04552a9841a980feb4305c89d2e8
Source dataset
uspto-grants-2011_07
Patent number
US07977332B2

Linked notes

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