Formamide → HCID 178518229, compound

HRID 1958007Notes

Reaction equation

HRID 1958007 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[S:5][C:6]=1[C:7]([O:9]C)=O.[CH:17]([NH2:19])=O>>[N:11]1([C:4]2[S:5][C:6]3[C:7](=[O:9])[N:19]=[CH:17][NH:1][C:2]=3[N:3]=2)[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1

Participants

3

Reactant 2

HCID 713FormamideHCID 2764112Methyl 4-amino-2-(morpholin-4-yl)-1,3-thiazole-5-carboxylate

Product 1

HCID 178518229HCID 178518229, compoundYield 93.2%

Conditions

Temperature
150 °C

Procedure

A sealed tube was charged with methyl 4-amino-2-(4-morpholinyl)-1,3-thiazole-5-carboxylate (4 g, 16.44 mmol) and formamide (40 mL, 1004 mmol). The reaction was heated at 150° C. overnight. The reaction mixture was cooled, filtered, and the solid was washed with DCM and MeOH. The solid was collected and dried under vacuum to give 3.65 g (93%) of product. LCMS (ES) m/z=239.0 (M+H)+, 1H NMR (400 MHz, DMSO-d6) δppm 12.4 (br s, 1H, NH), 8.10 (s, 1H) 3.72 (m, 4H). 3.58 (m, 4H).

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationfiltered
  3. washthe solid was washed with DCM and MeOH
  4. customThe solid was collected
  5. customdried under vacuum

Sources & evidence

ORD record
ord-f9835c4f0c054d57b9f5be2a8ffe2e80
Source dataset
uspto-grants-2013_04
Patent number
US08410095B2

Reaction notes

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