HCID 178485620, compound → (R)-N-(1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)pyrrolidin-3-yl)-2-(1H-imidazol-4-yl)-N-methylacetamide

HRID 527916Notes

Reaction equation

HRID 527916 reaction equation
[NH:1]1[CH:5]=[C:4]([CH2:6][C:7]([N:9]([CH3:32])[C@@H:10]2[CH2:14][CH2:13][N:12]([C:15]3[C:16]4[CH:23]=[CH:22][N:21](COCC[Si](C)(C)C)[C:17]=4[N:18]=[CH:19][N:20]=3)[CH2:11]2)=[O:8])[N:3]=[CH:2]1>C(O)(C(F)(F)F)=O.C(Cl)Cl>[N:18]1[C:17]2[NH:21][CH:22]=[CH:23][C:16]=2[C:15]([N:12]2[CH2:13][CH2:14][C@@H:10]([N:9]([CH3:32])[C:7](=[O:8])[CH2:6][C:4]3[N:3]=[CH:2][NH:1][CH:5]=3)[CH2:11]2)=[N:20][CH:19]=1

Participants

4

Reactant 1

HCID 178485620HCID 178485620, compound

Product 1

HCID 178485621(R)-N-(1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)pyrrolidin-3-yl)-2-(1H-imidazol-4-yl)-N-methylacetamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of (R)-2-(1H-imidazol-4-yl)-N-methyl-N-(1-(7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)pyrrolidin-3-yl)acetamide (0.11 mmol) in TFA (1 mL) and DCM (2 mL) was stirred at room temperature for 1.5 hours. The volatiles were removed under reduce pressure. The residue was dissolved in MeOH (2 mL) and treated with ethane-1,2-diamine (0.2 mL) at room temperature overnight. The volatiles were then removed under reduced pressure and the residue was purified by flash chromatography to give the title compound. MS (m/z): 326 (M+H)+.

Workup

  1. customThe volatiles were removed
  2. dissolutionThe residue was dissolved in MeOH (2 mL)
  3. additiontreated with ethane-1,2-diamine (0.2 mL) at room temperature overnight
  4. customThe volatiles were then removed under reduced pressure
  5. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-b897ba591d524f1499e33095287e999e
Source dataset
uspto-grants-2016_05
Patent number
US09346810B2

Reaction notes

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