Water → HCID 90411819, compound

HRID 1850696Notes

Reaction equation

HRID 1850696 reaction equation
[H-].[Na+].[Br:3][C:4]1[C:5]([CH3:10])=[N:6][S:7][C:8]=1N.[NH2:11][C:12]1[C:21]([C:22]([O:24]N2C3C=C(Cl)C=CC=3N=N2)=[O:23])=[C:15]2[N:16]=[CH:17][C:18]([F:20])=[CH:19][N:14]2[N:13]=1.O>CN1C(=O)CCC1>[NH2:11][C:12]1[C:21]([C:22]([O:24][C:8]2[S:7][N:6]=[C:5]([CH3:10])[C:4]=2[Br:3])=[O:23])=[C:15]2[N:16]=[CH:17][C:18]([F:20])=[CH:19][N:14]2[N:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 177499314-Bromo-3-methyl-1,2-thiazol-5-amineHCID 86720889HCID 86720889, compound

Product 1

HCID 90411819HCID 90411819, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

NaH (210.3 mg, 5.259 mmol) was added to a solution of 4-bromo-3-methyl-isothiazol-5-amine (533 mg, 2.761 mmol) in dry NMP (21.95 mL) at RT. The solution was stirred at RT for 5 min before (6-chlorobenzotriazol-1-yl) 2-amino-6-fluoro-pyrazolo[1,5-a]pyrimidine-3-carboxylate 6a* (914.4 mg, 2.630 mmol) was added. After 10 min, the reaction mixture was treated with water (120 mL) and stirred for 15 mins. The pale brown solid was filtered off and dried in vacuo to afford 4-bromo-3-methylisothiazol-5-yl 2-amino-6-fluoropyrazolo[1,5-a]pyrimidine-3-carboxylate. (801 mg, 82%). MS (ES+) 370.5.

Workup

  1. additionwas added
  2. filtrationThe pale brown solid was filtered off
  3. customdried in vacuo

Sources & evidence

ORD record
ord-4912994b3abc4374bbf0f163990528c3
Source dataset
uspto-grants-2015_02
Patent number
US08957078B2

Reaction notes

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