Hydrochloric Acid → HCID 71726649, compound

HRID 870946Notes

Reaction equation

[C:1]([C:3]1[C:8]([O:9][CH2:10][C@@H:11]([NH:16]C(=O)OC(C)(C)C)[CH2:12][CH:13]([CH3:15])[CH3:14])=[CH:7][C:6]2[O:24][CH:25]([CH3:32])[C:26]3[C:31]([C:5]=2[CH:4]=1)=[CH:30][CH:29]=[N:28][CH:27]=3)#[N:2].Cl.O1CCOCC1>ClCCl>[NH2:16][C@@H:11]([CH2:12][CH:13]([CH3:15])[CH3:14])[CH2:10][O:9][C:8]1[C:3]([C:1]#[N:2])=[CH:4][C:5]2[C:31]3[C:26](=[CH:27][N:28]=[CH:29][CH:30]=3)[CH:25]([CH3:32])[O:24][C:6]=2[CH:7]=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, 2H), 8.58 (s, 1H), 8.34 (d, J=6 Hz, 1H), 7.01 (s, 1H), 5.74 (t, J=6.4 Hz, 1H), 4.48 (m, 1H), 4.33 (m, 1H), 3.78 (m, 1H), 1.82-1.68 (m, 6H), 1.06 (m, 6H). 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-c36dc2e9317b412ca944348db1609466
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969564B2

Reaction notes

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