Methanesulfonic Acid → HCID 86641695, compound

HRID 2060736Notes

Reaction equation

HRID 2060736 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([C:15]3[CH:16]=[N:17][N:18]([CH3:20])[CH:19]=3)[CH:10]=2)[C:5]([CH3:21])=[CH:4][C:3]=1[NH:22][C:23]([C:25]1([C:28]([NH:30][C:31]2[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=2)=[O:29])[CH2:27][CH2:26]1)=[O:24].[CH3:38][S:39]([OH:42])(=[O:41])=[O:40]>C(Cl)Cl>[CH3:38][S:39]([OH:42])(=[O:41])=[O:40].[F:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([C:15]3[CH:16]=[N:17][N:18]([CH3:20])[CH:19]=3)[CH:10]=2)[C:5]([CH3:21])=[CH:4][C:3]=1[NH:22][C:23]([C:25]1([C:28]([NH:30][C:31]2[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=2)=[O:29])[CH2:26][CH2:27]1)=[O:24]

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 67408303HCID 67408303, compound

Product 1

HCID 86641695HCID 86641695, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-(2-fluoro-5-methyl-4-(2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yloxy)phenyl)-N′-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide (0.067 g, 0.133 mmol) was dissolved in CH2Cl2 (1 ml), 1.0 M methanesulfonic acid (0.133 ml, 0.133 mmol) was added and the reaction mixture was stirred at RT for 1 hour. The solid was filtered to obtain N-(2-fluoro-5-methyl-4-(2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yloxy)phenyl)-N′-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide methanesulfonate salt (55 mg, 67% yield). 1H NMR (400 MHz, DMSO-d6): δ 10.8 (brs, 1H), 9.81 (s, 1H), 8.53 (m, 2H), 8.18 (m, 1H), 8.01 (m, 1H), 7.57 (m, 3H), 7.32 (m, 1H), 7.16 (m, 2H), 6.94 (m, 1H), 3.90 (s, 3H), 2.29 (s, 3H), 2.09 (s, 3H), 1.5-1.7 (m, 4H).

Workup

  1. filtrationThe solid was filtered

Sources & evidence

ORD record
ord-da94d3402a4b47c482957fdac5786413
Source dataset
uspto-grants-2012_10
Patent number
US08278331B2

Reaction notes

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