Ammonia → HCID 59728123, compound

HRID 2043323Notes

Reaction equation

HRID 2043323 reaction equation
CN(C)S([N:6]1[C:10]([CH2:11][NH:12][CH2:13][CH3:14])=[CH:9][N:8]=[CH:7]1)(=O)=O.[Cl:16][C:17]1[CH:22]=[C:21](F)[CH:20]=[CH:19][N:18]=1.Cl.N>C(O)C>[Cl:16][C:17]1[CH:22]=[C:21]([N:12]([CH2:13][CH3:14])[CH2:11][C:10]2[NH:6][CH:7]=[N:8][CH:9]=2)[CH:20]=[CH:19][N:18]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 27827922-Chloro-4-fluoropyridineHCID 66751381HCID 66751381, compound

Product 1

HCID 59728123HCID 59728123, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 5-ethylaminomethyl-imidazole-1-sulfonic acid dimethylamide (0.2 g, 0.86 mmol) and 2-chloro-4-fluoropyridine (0.12 g; 0.91 mmol) was heated in a sealed vessel in a microwave oven for 30 min at 140° C. Then after cooling a solution of hydrochloric acid in ethanol (5 N, 1 ml) was added and the mixture was stirred at 90° C. overnight. For workup aqueous ammonia solution was added to basic pH and the mixture was extracted three times with ethyl acetate. The combined organic layers were dried over magnesium sulfate and evaporated. The residue was purified by flash chromatography (SiO2; ethyl acetate/methanol 8:2) to yield a white solid, (0.13 g, 64%); MS (ISP): 239.0 ((M+H)+.).

Workup

  1. additionwas added
  2. extractionthe mixture was extracted three times with ethyl acetate
  3. dry with materialThe combined organic layers were dried over magnesium sulfate
  4. customevaporated
  5. customThe residue was purified by flash chromatography (SiO2; ethyl acetate/methanol 8:2)
  6. customto yield a white solid, (0.13 g, 64%)

Sources & evidence

ORD record
ord-6063835c8d5b4f9b90312f653ea67612
Source dataset
uspto-grants-2013_11
Patent number
US08586617B2

Reaction notes

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