Diisopropylethylamine → 4-chloro-1,3-dimethyl-N-[(4R)-2-phenylimidazo[1,2-a]pyrimidin-7-yl]-1H-pyrazole-5-carboxamide

HRID 1958313Notes

Reaction equation

[Cl:1][C:2]1[C:6]([CH3:7])=[N:5][N:4]([CH3:8])[C:3]=1[C:9]([OH:11])=O.C(N(C(C)C)CC)(C)C.[C:21]1([C:27]2[N:28]=[C:29]3[N:34]=[C:33]([NH2:35])[CH:32]=[CH:31][N:30]3[CH:36]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(OCC)(=O)C>[C:21]1([C:27]2[N:28]=[C:29]3[N:34]=[C:33]([NH:35][C:9]([C:3]4[N:4]([CH3:8])[N:5]=[C:6]([CH3:7])[C:2]=4[Cl:1])=[O:11])[CH:32]=[CH:31][N:30]3[CH:36]=2)[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

Conditions

Temperature: 0 °C

Procedure

4-Chloro-2,5-dimethyl-2H-pyrazole-3-carboxylic acid (100 mg, 0.57 mmol) and diisopropylethylamine (369 mg, 2.86 mmol) were added to a solution of 2-phenyl-imidazo[1,2-a]pyrimidin-7-ylamine (example 1, step 1, 100 mg, 0.48 mmol) in ethyl acetate (3 ml). At 0° C., propylphosphonic acid anhydride (1-propanephosphonic acid cyclic anhydride, 50% in ethyl acetate, 0.7 ml, 2.5 eq.) was added dropwise to the mixture. After stirring for 30 min at 0° C., the mixture was stirred overnight at RT. The mixture was taken up in ethyl acetate, washed (water), dried (Na2SO4), and concentrated under reduced pressure. The title compound (16 mg, 9%) was obtained from the residue by preparative HPLC (254 nm, Agilent Zorbax XdB-C18, Run: 7 min, Flow: 30 ml/min, Gradient: 0.0 min: 95/5 H2O/CH3CN; 0.5 min: 95/5 H2O/CH3CN 4.5 min: 5/95 H2O/CH3CN; 6.9 min 5/95 H2O/CH3CN; 7 min 95/5 H2O/CH3CN).

Workup

stirringthe mixture was stirred overnight at RT
washwashed (water)
dry with materialdried (Na2SO4)
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-c0289ffcb77d41f88b754720dd96249b
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08410117B2

Reaction notes

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