1-Methyl-5-(tri-n-butylstannyl)imidazole → HCID 90411751, compound

HRID 1850702Notes

Reaction equation

HRID 1850702 reaction equation
[NH2:1][C:2]1[C:11]([C:12]([NH:14][C:15]2[S:19][N:18]=[C:17]([CH3:20])[C:16]=2Br)=[O:13])=[C:5]2[N:6]=[CH:7][C:8]([F:10])=[CH:9][N:4]2[N:3]=1.C([Sn](CCCC)(CCCC)[C:27]1[N:28]([CH3:32])[CH:29]=[N:30][CH:31]=1)CCC>CN(C=O)C>[NH2:1][C:2]1[C:11]([C:12]([NH:14][C:15]2[S:19][N:18]=[C:17]([CH3:20])[C:16]=2[C:27]2[N:28]([CH3:32])[CH:29]=[N:30][CH:31]=2)=[O:13])=[C:5]2[N:6]=[CH:7][C:8]([F:10])=[CH:9][N:4]2[N:3]=1

Participants

4

Reactant 2

HCID 109156511-Methyl-5-(tri-n-butylstannyl)imidazoleHCID 90411776HCID 90411776, compound

Product 1

HCID 90411751HCID 90411751, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

2-amino-N-(4-bromo-3-methyl-isothiazol-5-yl)-6-fluoro-pyrazolo[1,5-a]pyrimidine-3-carboxamide (20 mg, 0.05388 mmol), tributyl-(3-methylimidazol-4-yl)stannane (40.01 mg, 0.1078 mmol) dichloropalladium triphenylphosphane (7.566 mg, 0.01078 mmol) in DMF (2 mL) was degassed for 5 min, then heated at 110° C. After 2 h, the reaction mixture was loaded on a SCX column, washed with DCM/MeOH mixtures. The product was eluted with a 2M solution of ammonia in MeOH and the eluent was concentrated in vacuo. The residue was purified by fractionlynx to yield 2-amino-6-fluoro-N-(3-methyl-4-(1-methyl-1H-imidazol-5-yl)isothiazol-5-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide as a pale yellow solid. (8.09 mg, 37.4%). MS (ES+) 373.1.

Workup

  1. washwashed with DCM/MeOH mixtures
  2. washThe product was eluted with a 2M solution of ammonia in MeOH
  3. concentrationthe eluent was concentrated in vacuo
  4. customThe residue was purified by fractionlynx

Sources & evidence

ORD record
ord-33fa8d8599084a44b425a99e09700403
Source dataset
uspto-grants-2015_02
Patent number
US08957078B2

Reaction notes

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