1-[2-Chloro-1-hydroxy-2-(1-quinolin-6-ylcyclopropyl)ethyl]pyrrolidine-2,5-dione → tert-butyl 3-[3-(1-quinolin-6-ylcyclopropyl)imidazo[1,2-a]pyrimidin-6-yl]-1H-pyrazol-1-ylacetate

HRID 1257925Notes

Reaction equation

[C:1]([O:5][C:6](=[O:20])[CH2:7][N:8]1[CH:12]=[CH:11][C:10]([C:13]2[CH:14]=[N:15][C:16]([NH2:19])=[N:17][CH:18]=2)=[N:9]1)([CH3:4])([CH3:3])[CH3:2].Cl[CH:22]([C:32]1([C:35]2[CH:36]=[C:37]3[C:42](=[CH:43][CH:44]=2)[N:41]=[CH:40][CH:39]=[CH:38]3)[CH2:34][CH2:33]1)[CH:23](N1C(=O)CCC1=O)O>C(O)C>[C:1]([O:5][C:6](=[O:20])[CH2:7][N:8]1[CH:12]=[CH:11][C:10]([C:13]2[CH:14]=[N:15][C:16]3[N:17]([C:22]([C:32]4([C:35]5[CH:36]=[C:37]6[C:42](=[CH:43][CH:44]=5)[N:41]=[CH:40][CH:39]=[CH:38]6)[CH2:34][CH2:33]4)=[CH:23][N:19]=3)[CH:18]=2)=[N:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 105 °C

Procedure

A mixture of tert-butyl[3-(2-aminopyrimidin-5-yl)-1H-pyrazol-1-yl]acetate (16 mg, 0.058 mmol) and 1-[2-chloro-1-hydroxy-2-(1-quinolin-6-ylcyclopropyl)ethyl]pyrrolidine-2,5-dione (20 mg, 0.058 mmol) in ethanol (0.3 mL) was stirred overnight at 105° C. The reaction mixture was purified by RP-HPLC (pH 10) to afford the desired product (10 mg, 37%). LCMS: (M+H)=467.0.

Workup

customThe reaction mixture was purified by RP-HPLC (pH 10)

Sources & evidence

ORD record: ord-f37c97dc5aa443aa803335cb223789c7
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08461330B2

Reaction notes

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