Hydrochloric Acid → HCID 71726649, compound

HRID 2369536Notes

Reaction equation

C(OC(=O)[NH:7][C@@H:8]([CH2:28][CH:29]([CH3:31])[CH3:30])[CH2:9][O:10][C:11]1[C:12]([C:26]#[N:27])=[CH:13][C:14]2[C:24]3[C:19](=[CH:20][N:21]=[CH:22][CH:23]=3)[CH:18]([CH3:25])[O:17][C:15]=2[CH:16]=1)(C)(C)C.Cl.O1CCOCC1>ClCCl>[NH2:7][C@@H:8]([CH2:28][CH:29]([CH3:31])[CH3:30])[CH2:9][O:10][C:11]1[C:12]([C:26]#[N:27])=[CH:13][C:14]2[C:24]3[C:19](=[CH:20][N:21]=[CH:22][CH:23]=3)[CH:18]([CH3:25])[O:17][C:15]=2[CH:16]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of tert-butyl((2S)-1-((9-cyano-5-methyl-5H-chromeno[3,4-c]pyridin-8-yl)oxy)-4-methylpentan-2-yl)carbamate (15 mg, 0.034 mmol) in dichloromethane (2 mL) cooled to 0° C. was added HCl, 4M in dioxane (1.0 mL, 4.00 mmol) slowly over a period of 1 min. The reaction mixture was stirred at 0° C. for 5 min and then warmed to room temperature and allowed to stir for 2 h. The solvents were removed under reduced pressure and the crude material was washed with 5% methanol in ethyl acetate to afford 8-(((S)-2-amino-4-methylpentyl)oxy)-5-methyl-5H-chromeno[3,4-c]pyridine-9-carbonitrile (9 mg, 0.025 mmol, 73% yield) as a yellow solid. 1H NMR (400 MHz, MeOD) δ 8.74 (bs, 2 H), 8.58 (s, 1 H), 8.34 (d, J=6 Hz, 1 H), 7.01 (s, 1 H), 5.74 (t, J=6.4 Hz, 1 H), 4.48 (m, 1 H), 4.33 (m, 1 H), 3.78 (m, 1 H), 1.82-1.68 (m, 6 H), 1.06 (m, 6 H). LCMS (ESI) m/e 338.2 [(M+H)+, calcd for C20H24N3O2 338.2] LC/MS retention time (method D): tR=1.17 min. HPLC retention time (method A): tR=7.97 min and 8.03 min (diastereomeric mixture); HPLC retention time (method B): tR=8.77 min (peaks overlapped).

Workup

temperaturewarmed to room temperature
stirringto stir for 2 h
customThe solvents were removed under reduced pressure
washthe crude material was washed with 5% methanol in ethyl acetate

Sources & evidence

ORD record: ord-236943a3605c45f8ae231a861916ceff
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08703953B2

Reaction notes

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