Lithium hydroxide, monohydrate → HCID 57378225, compound

HRID 72548Notes

Reaction equation

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

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of methyl 6-((5-chloro-2-(3-(3-fluorophenoxy)azetidin-1-yl)nicotinamido)methyl)nicotinate (D160) (40.5 mg, 0.079 mmol) in a mixture 1-4 dioxane/water (1.5 ml/0.5 ml), lithium hydroxide hydrate (10 mg, 0.24 mmol) was added. The reaction mixture was heated to 70° C. under microwave irradiation for 20 min (4 cycles of 5 min each). After solvent evaporation the residue was taken in water (5 ml) and 1M HCl (5 ml) and extracted with ethylacetate (3×10 ml). Collected organics after solvent evaporation afforded the title compound (E25) (29 mg)

Workup

customAfter solvent evaporation the residue
extraction1M HCl (5 ml) and extracted with ethylacetate (3×10 ml)
customCollected organics after solvent evaporation

Sources & evidence

ORD record: ord-ada535df02a6488d8a953beb9d8546f4
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08828987B2

Reaction notes

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