Sodium Hydroxide → HCID 68157348, compound

HRID 537566Notes

Reaction equation

[Cl:1][C:2]1[C:3]([CH3:31])=[N:4][N:5]([C:7]2[N:12]=[CH:11][C:10]([NH:13][CH:14]([CH:26]3[CH2:30][CH2:29][CH2:28][CH2:27]3)[C:15]3[CH:25]=[CH:24][C:18]([C:19]([O:21]CC)=[O:20])=[CH:17][CH:16]=3)=[CH:9][CH:8]=2)[CH:6]=1.[OH-].[Na+]>CO.O1CCCC1>[Cl:1][C:2]1[C:3]([CH3:31])=[N:4][N:5]([C:7]2[N:12]=[CH:11][C:10]([NH:13][CH:14]([CH:26]3[CH2:30][CH2:29][CH2:28][CH2:27]3)[C:15]3[CH:25]=[CH:24][C:18]([C:19]([OH:21])=[O:20])=[CH:17][CH:16]=3)=[CH:9][CH:8]=2)[CH:6]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of (+/−)-ethyl 4-((6-(4-chloro-3-methyl-1H-pyrazol-1-yl)pyridin-3-ylamino)(cyclopentyl)methyl)benzoate (78.6 mg, 0.179 mmol) in methanol (1 mL) and tetrahydrofuran (1 mL) was added 1 N aqueous sodium hydroxide (0.36 mL, 0.36 mmol). The reaction was heated to 50° C. for 10 minutes. The heat was removed and the reaction was allowed to stir at room temperature for 1 hour. The reaction was concentrated. The residue was taken up in water and acidified to pH=4 with 1 N aqueous hydrochloric acid. The resulting precipitate was collected by filtration and dried under vacuum to give the title compound (68.3 mg, 93%) as a white solid. 1H NMR (400 MHz, CD3OD, δ): 8.19 (s, 1H), 7.92-7.96 (m, 2H), 7.66-7.69 (m, 1H), 7.48 (d, J=8.4 Hz, 2H), 7.42-7.45 (m, 1H), 7.03 (dd, J=8.9, 2.8 Hz, 1H), 4.18 (d, J=9.2 Hz, 1H), 2.22 (s, 3H), 1.98-2.07 (m, 1H), 1.43-1.74 (m, 6H), 1.23-1.38 (m, 2H). MS (M+1) 411.3.

Workup

customThe heat was removed
concentrationThe reaction was concentrated
filtrationThe resulting precipitate was collected by filtration
customdried under vacuum

Sources & evidence

ORD record: ord-1a9dbf8ea9a541819a8504698951c744
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08859591B2

Reaction notes

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