Pyrrolidine → HCID 51034365, compound

HRID 2382729Notes

Reaction equation

HRID 2382729 reaction equation
CN(C(O[N:9]1N=NC2C=[CH:13][CH:14]=[CH:15][C:10]1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(C(C)C)CC)(C)C.[CH3:32][N:33]1[C:37]([C:38](=[O:55])[NH:39][C:40]2[CH:45]=[CH:44][N:43]3[CH:46]=[C:47]([C:49]4[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=4)[N:48]=[C:42]3[CH:41]=2)=[C:36]([C:56](O)=[O:57])[CH:35]=[N:34]1.N1CCCC1>CN(C=O)C.O>[C:49]1([C:47]2[N:48]=[C:42]3[CH:41]=[C:40]([NH:39][C:38]([C:37]4[N:33]([CH3:32])[N:34]=[CH:35][C:36]=4[C:56]([N:9]4[CH2:10][CH2:15][CH2:14][CH2:13]4)=[O:57])=[O:55])[CH:45]=[CH:44][N:43]3[CH:46]=2)[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=1

Participants

7

Reactant 4

HCID 31268PyrrolidineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 67041900HCID 67041900, compound

Product 1

HCID 51034365HCID 51034365, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

TBTU (75 mg) and diisopropylethylamine (75 mg) were added to a solution of 1-methyl-5-(2-phenyl-imidazo[1,2-a]pyridin-7-ylcarbamoyl)-1H-pyrazole-4-carboxylic acid (70 mg) in DMF (2 ml), and the mixture was stirred at r.t. (30 min). Pyrrolidine (14 mg) was added to the brown solution, and the reaction mixture was stirred at r.t. overnight. Water was added and the mixture was extracted several times with ethyl acetate. The combined organic layers were dried (Na2SO4), and evaporated. The title compound (43 mg, 54%) was isolated from the residue by preparative, inverse-phase HPLC (Agilent Zorbax XdB-C18 column, time per run ˜7 min, flow rate 30 ml/min, solvent gradient H2O/CH3CN=95:5-5:95). MS (m/e)=415.3 [M+H+].

Workup

  1. stirringthe reaction mixture was stirred at r.t. overnight
  2. extractionthe mixture was extracted several times with ethyl acetate
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. customevaporated

Sources & evidence

ORD record
ord-87a95b38d4fb42d696a17e4e43b58d97
Source dataset
uspto-grants-2012_09
Patent number
US08263584B2

Reaction notes

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