Sodium Chloride → (2Z)-3-(5-chloro-6-{[(3R)-1-(cyclohexylmethyl)-3-piperidinyl]amino}-3-pyridinyl)-2-fluoroacrylic acid

HRID 226389Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4](/[CH:22]=[C:23](\[F:29])/[C:24]([O:26]CC)=[O:25])[CH:5]=[N:6][C:7]=1[NH:8][C@@H:9]1[CH2:14][CH2:13][CH2:12][N:11]([CH2:15][CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[CH2:10]1.[OH-].[Na+].[Na+].[Cl-]>CO>[Cl:1][C:2]1[CH:3]=[C:4](/[CH:22]=[C:23](\[F:29])/[C:24]([OH:26])=[O:25])[CH:5]=[N:6][C:7]=1[NH:8][C@@H:9]1[CH2:14][CH2:13][CH2:12][N:11]([CH2:15][CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[CH2:10]1

Participants

Conditions

Temperature: 60 °C

Procedure

The mixture of ethyl (2Z)-3-(5-chloro-6-{[(3R)-1-(cyclohexylmethyl)-3-piperidinyl]amino}-3-pyridinyl)-2-fluoroacrylate (0.73 g) and 1N-NaOH (3.44 mL) in MeOH (20 mL) was stirred at 60° C. for 3 hr. To the reaction mixture was added 1N-NaCl 3.44 mL and the mixture was evaporated in vacuo to give (2Z)-3-(5-chloro-6-{[(3R)-1-(cyclohexylmethyl)-3-piperidinyl]amino}-3-pyridinyl)-2-fluoroacrylic acid (0.68 g).

Workup

customthe mixture was evaporated in vacuo

Sources & evidence

ORD record: ord-ac97e44bd812410a8262d22a83d54bbf
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07557127B2

Reaction notes

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