Diisopropylethylamine → 4-(Azetidine-1-carbonyl)-2-methyl-2H-pyrazole-3-carboxylic acid (6-cyclopropyl-2-phenyl-imidazo[1,2-a]pyridin-7-yl)-amide

HRID 908234Notes

Reaction equation

CCCP(=O)=O.[CH:7]1([C:10]2[C:11]([NH2:25])=[CH:12][C:13]3[N:14]([CH:16]=[C:17]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[N:18]=3)[CH:15]=2)[CH2:9][CH2:8]1.[N:26]1([C:30]([C:32]2[CH:36]=[N:35][N:34]([CH3:37])[C:33]=2[C:38](O)=[O:39])=[O:31])[CH2:29][CH2:28][CH2:27]1.C(N(CC)C(C)C)(C)C>C(OCC)(=O)C>[CH:7]1([C:10]2[C:11]([NH:25][C:38]([C:33]3[N:34]([CH3:37])[N:35]=[CH:36][C:32]=3[C:30]([N:26]3[CH2:29][CH2:28][CH2:27]3)=[O:31])=[O:39])=[CH:12][C:13]3[N:14]([CH:16]=[C:17]([C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=4)[N:18]=3)[CH:15]=2)[CH2:9][CH2:8]1

Participants

Conditions

Temperature: 0 °C

Procedure

Propylphosphonic anhydride solution (50% in ethyl acetate, 0.59 ml) was added to a cooled (0° C.) solution of 6-cyclopropyl-2-phenyl-imidazo[1,2-a]pyridin-7-ylamine (100 mg, 0.40 mmol), 4-(azetidine-1-carbonyl)-2-methyl-2H-pyrazole-3-carboxylic acid (Step 3, 167 mg, 0.51 mmol), and N,N-diisopropylethylamine (311 mg) in ethyl acetate (3 ml). The mixture was stirred for 30 min at 0° C. and overnight at r.t. The reaction mixture was taken up in ethyl acetate, washed with water, dried (Na2SO4) and evaporated. The title compound (31 mg, 18%) 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)=441.3 [M+H+].

Workup

washwashed with water
dry with materialdried (Na2SO4)
customevaporated

Sources & evidence

ORD record: ord-117f33447b3d445f90e79596d620c569
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08017604B2

Reaction notes

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