Hydrochloric Acid → HCID 44538990, compound

HRID 449031Notes

Reaction equation

C(OC([N:8]1[CH2:11][CH:10]([C:12]2[N:16]3[CH:17]=[CH:18][N:19]=[C:20]([NH2:21])[C:15]3=[C:14]([C:22]3[CH:27]=[CH:26][C:25]([O:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[CH:24][CH:23]=3)[N:13]=2)[CH2:9]1)=O)(C)(C)C.Cl>O1CCOCC1>[NH:8]1[CH2:9][CH:10]([C:12]2[N:16]3[CH:17]=[CH:18][N:19]=[C:20]([NH2:21])[C:15]3=[C:14]([C:22]3[CH:27]=[CH:26][C:25]([O:28][C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=4)=[CH:24][CH:23]=3)[N:13]=2)[CH2:11]1

Participants

Conditions

Temperature: 0 °C

Procedure

Into a round bottom flask at 0° C. was added 3-[8-amino-1-(4-phenoxyphenyl)-imidazo[1,5-a]pyrazin-3-yl]-azetidine-1-carboxylic acid tert-butyl ester (30 mg, 0.00006 mol) and 4 M of HCl in 1,4-Dioxane (2 mL) and the suspension was stirred at 0° C.→RT for 3-4 h. The solvent was concentrated in vacuo and purification by prep TLC using 10% NH3 in MeOH in DCM afforded the compound as a yellow solid. The compound was dissolved in MeOH and passed through an SPE cartridge. The compound was registered as OSIP 700588 AA. 1H NMR (400 MHz, CDCl3): δ=4.17-4.28 (m, 2H), 4.42 (d, J=3.03 Hz, 3H), 7.05-7.10 (m, 2H), 7.10-7.15 (m, 3H), 7.15-7.19 (m, 1H), 7.20 (d, J=5.05 Hz, 1H), 7.34-7.41 (m, 2H), 7.55-7.65 (m, 2H). MS (ES+): m/z 358.12 [MH+]. HPLC: tR=0.65 min (Open Lynx, polar—5 min).

Workup

concentrationThe solvent was concentrated in vacuo and purification by prep TLC

Sources & evidence

ORD record: ord-cf7e15a5d91b4aa6b35f6fc994fd41d4
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08481733B2

Reaction notes

Loading…