Potassium Carbonate → HCID 68546393, compound

HRID 1446741Notes

Reaction equation

[C:1]([O:5][C:6](=[O:31])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:19]3[CH:20]=[CH:21][C:22]([C:24]4[CH:25]=[N:26][C:27](F)=[CH:28][CH:29]=4)=[CH:23][C:18]3=[N:17][CH:16]=2)=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:32][N:33]1[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]1.C([O-])([O-])=O.[K+].[K+]>CS(C)=O>[C:1]([O:5][C:6](=[O:31])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:19]3[CH:20]=[CH:21][C:22]([C:24]4[CH:25]=[N:26][C:27]([N:36]5[CH2:37][CH2:38][N:33]([CH3:32])[CH2:34][CH2:35]5)=[CH:28][CH:29]=4)=[CH:23][C:18]3=[N:17][CH:16]=2)=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

Dissolve {4-[7-(6-fluoro-pyridin-3-yl)-imidazo[1,2-a]pyridin-3-yl]-benzyl}-carbamic acid tert-butyl ester (0.500 g, 1.19 mmol, 1.0 eq.) and N-methyl piperazine (0.53 mL, 4.78 mmol, 4.0 eq.) in DMSO (20 mL). Add K2CO3 (0.330 g, 2.0 eq.). Stir the reaction mixture at 80° C. overnight. Pour the mixture into 20 mL of ice. Filter the solid, and purify by silica gel chromatography with a 0-5% MeOH/DCM gradient to give the title compound 0.408 g (0.82 mmol, 70%) as a slightly yellow solid. Use the solid directly in the reaction B below: MS(ES), m/z 499 (M+1).

Workup

filtrationFilter the solid
custompurify by silica gel chromatography with a 0-5% MeOH/DCM gradient

Sources & evidence

ORD record: ord-0ef51fca5498407c8e00d4a97c3b274f
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07666879B2

Reaction notes

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