Reaktion #1018399

Reaktionsgleichung

(R)-(1-(2-(1-(4-chloro-1H-pyrazol-1-yl)cyclopropyl)-3H-imidazo[4,5-b]pyridin-5-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanone

methanesulfonic acid

→

(R)-(1-(2-(1-(4-chloro-1H-pyrazol-1-yl)cyclopropyl)-3H-imidazo[4,5-b]pyridin-5-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanone methanesulfonate

Ausbeute 91.1%

Lösungsmittel

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationThe mixture was filtered
2. 2
   Waschenthe solids were rinsed with acetonitrile
3. 3
   SonstigeThe solids were collected
4. 4
   Sonstigedried under high vacuum for 1 h

Vorschrift

To a solution of (R)-(1-(2-(1-(4-chloro-1H-pyrazol-1-yl)cyclopropyl)-3H-imidazo[4,5-b]pyridin-5-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanone (Example 109-A, 56.49 g, 128.4 mmol) in acetonitrile (130 mL) was added methanesulfonic acid (8.33 mL, 128 mmol). The mixture was stirred for 18 h at room temperature. The mixture was filtered and the solids were rinsed with acetonitrile. The solids were collected and dried under high vacuum for 1 h to afford (R)-(1-(2-(1-(4-chloro-1H-pyrazol-1-yl)cyclopropyl)-3H-imidazo[4,5-b]pyridin-5-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanone methanesulfonate (62.5 g, 90%). 1H NMR (400 MHz, CDCl3) δ 1.65-1.75 (m, 1H), 1.84-2.13 (m, 11H), 2.75-2.85 (m, 1H), 2.87 (s, 3H), 3.28-3.35 (m, 1H), 3.39-3.57 (m, 4H), 3.65-3.72 (m, 1H), 4.02-4.09 (m, 1H), 4.11-4.17 (m, 1H), 6.73-6.82 (m, 1H), 7.55 (s, 1H), 7.76 (s, 1H), 8.13 (d, 1H); MS (ES+) (M+H) 440; UPLC retention time 0.47 min (Method N). mp=212-214° C. Anal. Calculated for C22H26ClN7O.CH4O3S: C, 51.53; H, 5.64; N, 18.29; Cl, 6.61; S, 5.98. Found: C, 51.28; H, 5.65; N, 18.19; Cl, 6.56; S, 5.96.

Quelle