HCID 54674188, compound → HCID 54674340, compound

HRID 2402743Notes

Reaction equation

[CH3:1][C@@:2]1([NH:20][C:21](=O)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C@@H:9]2[C@@H:5]([CH2:6][N:7]([C:10]3[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[N:11]=3)[CH2:8]2)[CH2:4][CH2:3]1>O1CCCC1>[CH2:21]([NH:20][C@:2]1([CH3:1])[C@@H:9]2[C@@H:5]([CH2:6][N:7]([C:10]3[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:17])[F:18])[N:11]=3)[CH2:8]2)[CH2:4][CH2:3]1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of N-{(3aR,4S,6aS)-4-methyl-2-[6-(trifluoromethyl)pyridin-2-yl]octahydrocyclopenta[c]pyrrol-4-yl}benzamide (180 mg, 0.462 mmol) from Example 15 in tetrahydrofuran (1 mL) was added dropwise borane tetrahydrofuran complex solution (1.387 mL, 1.387 mmol). The reaction was heated at 80° C. for 3 hours, quenched with 2 N HCl (0.5 mL) and then stirred for 1 hour. The reaction mixture was neutralized with aqueous sodium bicarbonate and extracted with dichloromethane. The combined organic washes were purified by silica gel chromatography using 1-10% methanol (2 N ammonia)/dichloromethane as eluent to give the title compound: 1H NMR (500 MHz, pyridine-d5) δ ppm 8.69 (d, J=8.0, 1H), 8.65 (d, J=7.4, 2H), 8.57-8.48 (m, 2H), 8.44 (t, J=7.3, 1H), 8.14 (d, J=7.2, 1H), 7.69 (d, J=8.6, 1H), 4.92-4.83 (m, 2H), 4.76-4.65 (m, 2H), 4.52-4.46 (m, 1H), 4.46-4.39 (m, 1H), 4.13-4.05 (m, 1H), 3.72 (dd, J=15.8, 7.9, 1H), 3.26 (dq, J=13.2, 8.3, 1H), 2.87-2.73 (m, 2H), 2.71-2.58 (m, 1H), 2.49 (dq, J=9.4, 5.0, 1H), 2.29 (s, 3H); MS (ESI+) m/z 376 (M+H)+.

Workup

customquenched with 2 N HCl (0.5 mL)
extractionextracted with dichloromethane
customThe combined organic washes were purified by silica gel chromatography

Sources & evidence

ORD record: ord-30a03f24f8cd4f1fbc146dbccada4ea9
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08796470B2

Reaction notes

Loading…