Lithium Hydroxide → HCID 178524007, compound

HRID 539928Notes

Reaction equation

[OH-].[Li+].[F:3][C:4]1[C:5]([NH:20][CH:21]2[CH:27]3[CH2:28][CH2:29][CH:23]([CH2:24][CH2:25][CH2:26]3)[CH:22]2[C:30]([O:32]C)=[O:31])=[N:6][C:7]([C:10]2[C:18]3[C:13](=[N:14][CH:15]=[C:16]([F:19])[CH:17]=3)[NH:12][N:11]=2)=[N:8][CH:9]=1>C1COCC1>[F:3][C:4]1[C:5]([NH:20][CH:21]2[CH:27]3[CH2:28][CH2:29][CH:23]([CH2:24][CH2:25][CH2:26]3)[CH:22]2[C:30]([OH:32])=[O:31])=[N:6][C:7]([C:10]2[C:18]3[C:13](=[N:14][CH:15]=[C:16]([F:19])[CH:17]=3)[NH:12][N:11]=2)=[N:8][CH:9]=1

Participants

Conditions

Temperature: 85 °C

Procedure

A solution of lithium hydroxide (2.10 mL of 2N solution, 4.15 mmol) was added to a stirred solution of racemic methyl 7-(5-fluoro-2-(5-fluoro-1H-pyrazolo[3,4-b]pyridin-3-yl)pyrimidin-4-ylamino)bicyclo[3.2.2]nonane-6-carboxylate, I-36, (0.18 g, 0.42 mmol) in THF (7 mL). The solution was heated at 85° C. for 6 hr and cooled to room temperature. The solution was concentrated in vacuo and water (5 mL) was added. The solution was slowly neutralized with 1N HCl to produce a white precipitate. The precipitate was filtered and washed with water (10 mL). The wet solid was lyophilized for 2 days to 112 mg of the desired product as a white powder: 1H NMR (400 MHz, CD3OD) δ 8.77 (s, 1H), 8.52 (s, 1H), 8.10 (s, 1H), 5.29 (m, 1H), 2.82 (m, 1H), 2.53 (m, 1H), 2.11-1.54 (brm, 10H), 1.29 (m, 1H); LC/MS Gradient 10-90%, 0.1% formic 5 min, C18/ACN, RT=2.33 minutes (M+H) 415.44.

Workup

temperaturecooled to room temperature
concentrationThe solution was concentrated in vacuo and water (5 mL)
additionwas added
customto produce a white precipitate
filtrationThe precipitate was filtered
washwashed with water (10 mL)
customLC/MS Gradient 10-90%, 0.1% formic 5 min

Sources & evidence

ORD record: ord-94d626e79035424e9fe7f974fc919f03
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871774B2

Reaction notes

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