Ammonium formate → HCID 178507109, compound

HRID 1969869Notes

Reaction equation

Cl.C([NH:9][C:10]12[CH2:17][CH2:16][C:13]([C:18]3[C:22]4=[C:23]5[CH:29]=[CH:28][NH:27][C:24]5=[N:25][CH:26]=[C:21]4[NH:20][N:19]=3)([CH2:14][CH2:15]1)[CH2:12][CH2:11]2)C1C=CC=CC=1.C([O-])=O.[NH4+]>CO>[C:18]1([C:13]23[CH2:16][CH2:17][C:10]([NH2:9])([CH2:15][CH2:14]2)[CH2:11][CH2:12]3)[C:22]2=[C:23]3[CH:29]=[CH:28][NH:27][C:24]3=[N:25][CH:26]=[C:21]2[NH:20][N:19]=1

Participants

Conditions

Temperature: 65 °C

Procedure

To a solution of N-benzyl-4-(3,6-dihydropyrazolo[4,3-d]pyrrolo[2,3-b]pyridin-1-yl)bicyclo[2.2.2]octan-1-amine hydrochloride (0.150 g, 0.368 mmol) in MeOH (6 mL) was added ammonium formate (0.116 g, 1.84 mmol) and 20% PdOH2 on carbon (0.039 g, 0.055 mmol). The reaction mixture was heated at about 65° C. for about 2 h. The reaction mixture was filtered through a pad of Celite® while washing with EtOAc (about 10 mL) and the solvent was removed under reduced pressure. Water and EtOAc (10 mL each) were added and the layers were separated. The aqueous layer was extracted with EtOAc (5×5 mL) and the combined organics were dried over anhydrous MgSO4, filtered, and concd under reduced pressure to give 4-(3,6-dihydropyrazolo[4,3-d]pyrrolo[2,3-b]pyridin-1-yl)bicyclo[2.2.2]octan-1-amine (0.073 g, 71%) as an off white foam: LC/MS (Table 1, Method b) Rt=1.08 min; MS m/z: 282 (M+H)+.

Workup

filtrationThe reaction mixture was filtered through a pad of Celite®
washwhile washing with EtOAc (about 10 mL)
customthe solvent was removed under reduced pressure
additionWater and EtOAc (10 mL each) were added
customthe layers were separated
extractionThe aqueous layer was extracted with EtOAc (5×5 mL)
dry with materialthe combined organics were dried over anhydrous MgSO4
filtrationfiltered

Sources & evidence

ORD record: ord-fbd2b31544164b3e8fca81f8608a2d39
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08426411B2

Reaction notes

Loading…