Methanesulfonic Acid → HCID 86647659, compound

HRID 1798705Notes

Reaction equation

HRID 1798705 reaction equation
[CH3:1][S:2]([OH:5])(=[O:4])=[O:3].[N:6]1[C:7]([CH2:15][O:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]3[C:27](=[O:28])[C:26]([CH3:30])([CH3:29])[O:25][C:24]=3[C:31]3[CH:38]=[CH:37][C:34]([C:35]#[N:36])=[CH:33][CH:32]=3)=[CH:19][CH:18]=2)=[CH:8][N:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=12>C(Cl)Cl.C(OCC)C>[CH3:1][S:2]([OH:5])(=[O:4])=[O:3].[N:6]1[C:7]([CH2:15][O:16][C:17]2[CH:18]=[CH:19][C:20]([C:23]3[C:27](=[O:28])[C:26]([CH3:30])([CH3:29])[O:25][C:24]=3[C:31]3[CH:32]=[CH:33][C:34]([C:35]#[N:36])=[CH:37][CH:38]=3)=[CH:21][CH:22]=2)=[CH:8][N:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=12

Participants

5

Reactant 2

HCID 6395Methanesulfonic AcidHCID 49779048HCID 49779048, compound

Product 1

HCID 86647659HCID 86647659, compoundYield 64.7%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

Methanesulfonic acid (309 mg, 3.2 mmol) was added to a solution of compound 4-(3-(4-(imidazo[1,2-a]pyridin-2-ylmethoxy)phenyl)-5,5-dimethyl-4-oxo-4,5-dihydrofuran-2-yl)benzonitrile (1.4 g, 3.2 mmol) in DCM (5 ml) and diethyl ether (30 mL) at RT under an atmosphere of nitrogen. The reaction mixture was stirred at RT for 4 h upon which it was filtered and the solids were washed with 20% DCM in diethyl ether and dried in vacuo to afford 4-(3-(4-(imidazo[1,2-a]pyridin-2-ylmethoxy)phenyl)-5,5-dimethyl-4-oxo-4,5-dihydrofuran-2-yl)benzonitrile methanesulfonate (1.1 g, 64%) as a white solid. 1H NMR: 500 MHz, DMSO-d6: δ 8.55 (d, 1H), 8.0 (s, 1H), 7.55 (Ar, 3H), 7.3-6.85 (Ar, 8H), 5.15 (s, 2H), 2.15 (s, 3H), 1.25 (s, 6H), HPLC: (98.5%, Condition-A).

Workup

  1. filtrationwas filtered
  2. washthe solids were washed with 20% DCM in diethyl ether
  3. customdried in vacuo

Sources & evidence

ORD record
ord-c21a7bb9c6d24b848f9b4d5e332e5b52
Source dataset
uspto-grants-2013_01
Patent number
US08343973B2

Reaction notes

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