Hydrochloric Acid → 5-[5-Bromo-4-(cyclopropylmethyl-amino)-pyrimidin-2-ylamino]-pyridine-2-sulfonic acid amide

HRID 1182053Notes

Reaction equation

HRID 1182053 reaction equation
[Br:1][C:2]1[C:3]([NH:9][CH2:10][CH:11]2[CH2:13][CH2:12]2)=[N:4][C:5](Cl)=[N:6][CH:7]=1.[NH2:14][C:15]1[CH:16]=[CH:17][C:18]([S:21]([NH2:24])(=[O:23])=[O:22])=[N:19][CH:20]=1.Cl.O>C(#N)C.O1CCOCC1>[Br:1][C:2]1[C:3]([NH:9][CH2:10][CH:11]2[CH2:13][CH2:12]2)=[N:4][C:5]([NH:14][C:15]2[CH:16]=[CH:17][C:18]([S:21]([NH2:24])(=[O:23])=[O:22])=[N:19][CH:20]=2)=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 223138505-Aminopyridine-2-sulfonamideHCID 58891001(5-Bromo-2-chloro-pyrimidin-4-yl)-cyclopropylmethyl-amine

Product 1

HCID 104535195-[5-Bromo-4-(cyclopropylmethyl-amino)-pyrimidin-2-ylamino]-pyridine-2-sulfonic acid amide

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

263 mg (1.0 mmol) of (5-bromo-2-chloro-pyrimidin-4-yl)-cyclopropylmethyl-amine is dissolved in 2 ml of acetonitrile and added to a suspension of 172 mg (1.0 mmol) of 5-amino-pyridine-2-sulfonic acid amide (representation according to W. T. Caldwell, E. C. Kornfeld J. Am. Chem. Soc. 1942, 64, 1695-1698) in 1 ml of acetonitrile, 0.25 ml of a 4 molar solution of hydrochloric acid in 1,4-dioxane as well as 0.25 ml of water. The reaction mixture is stirred under reflux overnight. After cooling, the precipitate that is formed is filtered off and washed with warm water. After drying, 286 mg (0.72 mmol, 72% of theory) of the product 5-[5-bromo-4-(cyclopropylmethyl-amino)-pyrimidin-2-ylamino]-pyridine-2-sulfonic acid amide is obtained.

Workup

  1. temperatureunder reflux overnight
  2. temperatureAfter cooling
  3. customthe precipitate that is formed
  4. filtrationis filtered off
  5. washwashed with warm water
  6. customAfter drying

Sources & evidence

ORD record
ord-bc58274207c24976b77aa43814b048b4
Source dataset
uspto-grants-2007_10
Patent number
US07288547B2

Reaction notes

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