Hydrochloric Acid → HCID 67414100, compound

HRID 2060731Notes

Reaction equation

HRID 2060731 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]([F:21])=[CH:4][C:3]=1[NH:22][C:23]([C:25]1([C:28]([NH:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[O:29])[CH2:27][CH2:26]1)=[O:24].[ClH:37].O1CCOCC1>C(#N)C>[ClH:37].[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]([F:21])=[CH:4][C:3]=1[NH:22][C:23]([C:25]1([C:28]([NH:30][C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)=[O:29])[CH2:27][CH2:26]1)=[O:24]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 46208890HCID 46208890, compound

Product 1

HCID 67414100HCID 67414100, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-(2,5-Difluoro-4-(2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yloxy)phenyl)-N′-phenylcyclopropane-1,1-dicarboxamide was dissolved in acetonitrile (5 ml) and 4M HCl in dioxane (0.068 ml, 0.274 mmol) was added slowly with stirring. The mixture was stirred for 1.5 hours at RT as a white solid slowly precipitated from the solution. The salt was collected via suction filtration and washed with diethyl ether. A suspension of the product in a 4:1 mix of acetonitrile and water was lyophilized overnight to obtain N-(2,5-difluoro-4-(2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yloxy)phenyl)-N′-phenylcyclopropane-1,1-dicarboxamide hydrochloride as a white powder (0.047 g, 65% yield). 1H NMR (400 MHz, DMSO-d6): δ 11.18 (s, 1H), 9.64 (s, 1H), 8.43 (m, 2H), 8.13 (m, 2H), 7.60 (m, 1H), 7.51 (m, 3H), 7.28 (m, 2H), 7.05 (m, 1H), 6.97 (broad s, 1H), 3.84 (s, 3H), 1.63 (m, 2H), 1.53 (m, 2H); MS (ESI) m/z: 490.2 (M+H+).

Workup

  1. stirringThe mixture was stirred for 1.5 hours at RT as a white solid
  2. customslowly precipitated from the solution
  3. filtrationThe salt was collected via suction filtration
  4. washwashed with diethyl ether
  5. additionA suspension of the product in a 4:1
  6. additionmix of acetonitrile and water

Sources & evidence

ORD record
ord-5d56f844ce0544dd9f3565914847f1da
Source dataset
uspto-grants-2012_10
Patent number
US08278331B2

Reaction notes

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