Sodium Hydroxide → HCID 57378435, compound

HRID 72552Notes

Reaction equation

HRID 72552 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5]([N:24]2[CH2:27][CH:26]([N:28]([C:30]3[CH:35]=[CH:34][C:33]([F:36])=[CH:32][C:31]=3[CH3:37])[CH3:29])[CH2:25]2)=[C:6]([CH:23]=1)[C:7]([NH:9][C:10]1([C:13]2[CH:22]=[CH:21][C:16]([C:17]([O:19]C)=[O:18])=[CH:15][CH:14]=2)[CH2:12][CH2:11]1)=[O:8].[OH-].[Na+]>C1OCCOC1.O>[Cl:1][C:2]1[CH:3]=[N:4][C:5]([N:24]2[CH2:25][CH:26]([N:28]([C:30]3[CH:35]=[CH:34][C:33]([F:36])=[CH:32][C:31]=3[CH3:37])[CH3:29])[CH2:27]2)=[C:6]([CH:23]=1)[C:7]([NH:9][C:10]1([C:13]2[CH:22]=[CH:21][C:16]([C:17]([OH:19])=[O:18])=[CH:15][CH:14]=2)[CH2:12][CH2:11]1)=[O:8]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67958583Methyl 4-(1-(5-chloro-2-(3-((4-fluoro-2-methylphenyl)(methyl)amino)azetidin-1-yl)nicotinamido)cyclopropyl)benzoate

Product 1

HCID 57378435HCID 57378435, compound

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
60 °C

Procedure

To a solution of starting from methyl 4-(1-(5-chloro-2-(3-((4-fluoro-2-methylphenyl)(methyl)amino)azetidin-1-yl)nicotinamido)cyclopropyl)benzoate (D171) (56 mg, 0.107 mmol). in a mixture 1-4 dioxane/water (3 ml/1 ml), 1N NaOH (0.16 ml) was added. The reaction mixture was stirred 2 h at 60° C. Organic solvent was evaporated in vacuo and the reaction mixture was acidified with 2N HCl (pH=2) and the resulting mixture was extracted with ethylacetate (3×5 ml). Combined organics were evaporated in vacuo to afford the title (E37) (53 mg).

Workup

  1. customOrganic solvent was evaporated in vacuo
  2. extractionthe resulting mixture was extracted with ethylacetate (3×5 ml)
  3. customCombined organics were evaporated in vacuo
  4. customto afford the title (E37) (53 mg)

Sources & evidence

ORD record
ord-efc178084d6d4edd8a0b96e426ed1a00
Source dataset
uspto-grants-2014_09
Patent number
US08828987B2

Reaction notes

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