5-Aminothiophene-2-sulfonamide → 4-[5-Bromo-4-(1-hydroxymethyl-propylamino)-pyrimidin-2-ylamino]-thiophene-2-sulfonic acid amide

HRID 1182057Notes

Reaction equation

HRID 1182057 reaction equation
[Br:1][C:2]1[C:3]([NH:9][C@H:10]([CH2:13][CH3:14])[CH2:11][OH:12])=[N:4][C:5](Cl)=[N:6][CH:7]=1.[NH2:15][C:16]1[CH:17]=[C:18]([S:21]([NH2:24])(=[O:23])=[O:22])[S:19][CH:20]=1.NC1SC(S(N)(=O)=O)=CC=1>C(O)C.Cl>[Br:1][C:2]1[C:3]([NH:9][CH:10]([CH2:11][OH:12])[CH2:13][CH3:14])=[N:4][C:5]([NH:15][C:16]2[CH:17]=[C:18]([S:21]([NH2:24])(=[O:23])=[O:22])[S:19][CH:20]=2)=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 247115985-Aminothiophene-2-sulfonamideHCID 450805884-Aminothiophene-2-sulfonamideHCID 58891316(R)-2-(2-chloro-5-bromopyrimidine-4-ylamino)butan-1-ol

Product 1

HCID 693321424-[5-Bromo-4-(1-hydroxymethyl-propylamino)-pyrimidin-2-ylamino]-thiophene-2-sulfonic acid amide

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

530 mg (1.9 mmol) of (R)-2-(5-bromo-2-chloro-pyrimidin-4-ylamino)-butan-1-ol is added to a suspension of 303 mg of a mixture that consists of 4-amino-thiophene-2-sulfonic acid amide and 5-amino-thiophene-2-sulfonic acid amide (ratio: 2:1) in 7 ml of ethanol and 170 μl of concentrated HCl. The reaction mixture is stirred for 21 hours under reflux. After cooling, the batch is purified by chromatography (Flashmaster II, hexane/EE 2:8). The crude product that is obtained is then recrystallized (ethyl acetate/diisopropyl ether). 47 mg (0.11 mmol, 7% of theory) of the product 4-[5-bromo-4-(1-hydroxymethyl-propylamino)-pyrimidin-2-ylamino]-thiophene-2-sulfonic acid amide is obtained.

Workup

  1. temperatureunder reflux
  2. temperatureAfter cooling
  3. customthe batch is purified by chromatography (Flashmaster II, hexane/EE 2:8)
  4. customThe crude product that is obtained
  5. customis then recrystallized (ethyl acetate/diisopropyl ether)

Sources & evidence

ORD record
ord-2da2ba2ba2ef4b8289ee8b1b82d63104
Source dataset
uspto-grants-2007_10
Patent number
US07288547B2

Reaction notes

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