Potassium Carbonate → HCID 71280821, compound

HRID 1497941Notes

Reaction equation

HRID 1497941 reaction equation
[F:1][C:2]1([F:36])[CH2:5][CH:4]([C:6]2[O:10][N:9]=[C:8]([C:11]3[CH:12]=[CH:13][C:14]([CH3:35])=[C:15]([NH:17][C:18]([C:20]4[N:24]5[CH:25]=[C:26]([C:29]6[N:33]=[C:32]([CH3:34])[NH:31][N:30]=6)[CH:27]=[CH:28][C:23]5=[N:22][CH:21]=4)=[O:19])[CH:16]=3)[N:7]=2)[CH2:3]1.Br[CH2:38][CH2:39][O:40][CH3:41].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[F:36][C:2]1([F:1])[CH2:5][CH:4]([C:6]2[O:10][N:9]=[C:8]([C:11]3[CH:12]=[CH:13][C:14]([CH3:35])=[C:15]([NH:17][C:18]([C:20]4[N:24]5[CH:25]=[C:26]([C:29]6[N:33]=[C:32]([CH3:34])[N:31]([CH2:38][CH2:39][O:40][CH3:41])[N:30]=6)[CH:27]=[CH:28][C:23]5=[N:22][CH:21]=4)=[O:19])[CH:16]=3)[N:7]=2)[CH2:3]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 809722-Bromoethyl methyl etherHCID 71280447HCID 71280447, compound

Product 1

HCID 71280821HCID 71280821, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-(5-(5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)-6-(5-methyl-1H-1,2,4-triazol-3-yl)imidazo[1,2-a]pyridine-3-carboxamide (F79) (6.0 mg, 0.012 mmol), 1-bromo-2-methoxyethane (1.7 mg, 0.012 mmol) and K2CO3(5.0 mg, 0.036 mmol) in DMF (0.5 mL) was heated at 120° C. for 30 minutes. The reaction mixture was purified by preparative HPLC to afford N-(5-(5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)-6-(1-(2-methoxyethyl)-5-methyl-1H-1,2,4-triazol-3-yl)imidazo[1,2-a]pyridine-3-carboxamide (F99). 1H NMR (400 MHz, d6-DMSO) δ 10.15 (s, 1H), 10.11 (m, 1H), 8.65 (s, 1H), 8.12 (d, J=1.6 Hz, 1H), 8.06 (dd, J=2.0, 9.2 Hz, 1H), 7.88 (dd, J=0.8, 9.2 Hz, 1H), 7.85 (dd, J=2.0, 8.0 Hz, 1H), 7.52 (d, J=8.0 Hz, 1H), 4.34 (t, J=5.2 Hz, 2H), 3.89 (m, 1H), 3.72 (t, J=5.2 Hz, 2H), 3.24 (s, 3H), 3.02-3.20 (m, 4H), 2.47 (s, 3H), 2.39 (s, 3H). MS m/z 549.1 (M+1)+.

Workup

  1. customThe reaction mixture was purified by preparative HPLC

Sources & evidence

ORD record
ord-ed6f9205a1e14c00a08064da285a436f
Source dataset
uspto-grants-2015_12
Patent number
US09199981B2

Reaction notes

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