m-Chloroperbenzoic acid → HCID 57961018, compound

HRID 449070Notes

Reaction equation

[CH:1]1([C:5]2[N:9]3[CH:10]=[CH:11][N:12]=[C:13]([NH2:14])[C:8]3=[C:7]([C:15]3[CH:20]=[CH:19][C:18]([S:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[CH:17][CH:16]=3)[N:6]=2)[CH2:4][CH2:3][CH2:2]1.ClC1C=CC=C(C(OO)=[O:36])C=1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:22]1([S:21]([C:18]2[CH:19]=[CH:20][C:15]([C:7]3[N:6]=[C:5]([CH:1]4[CH2:2][CH2:3][CH2:4]4)[N:9]4[CH:10]=[CH:11][N:12]=[C:13]([NH2:14])[C:8]=34)=[CH:16][CH:17]=2)=[O:36])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 3-cyclobutyl-1-(4-phenylsulfanylphenyl)-imidazo[1,5-a]pyrazin-8-ylamine (15.0 mg, 0.0403 mmol) in DCM (3 mL, 0.05 mol) at 0° C. was added a solution of m-chloroperbenzoic acid (10.4 mg, 0.0604 mmol) in DCM. The mixture was stirred at 0° C. for 30 min. Sat. aq. NaHCO3 solution was added to quench, and the material was transferred to a separatory funnel. The organic layer was concentrated in vacuo and redissolved in DMF (1 mL) for Gilson HPLC separation. The fractions containing the pure product were concentrated in vacuo to afford the title compound as a yellow solid. 1H NMR (400 MHz, CDCl3): δ=1.98-2.09 (m, 1H), 2.11-2.23 (m, 1H), 2.44-2.53 (m, 2H), 2.55-2.65 (m, 2H), 3.80 (t, J=8.5 Hz, 1H), 7.04 (d, J=5.3 Hz, 1H), 7.13 (d, J=5.3 Hz, 1H), 7.47-7.53 (m, 3H), 7.68-7.71 (m, 2H), 7.79 (s, 4H). MS (ES+): m/z 389.02 (100) [MH+]. HPLC: tR=2.17 min (Open Lynx, polar—5 min).

Workup

customto quench
customthe material was transferred to a separatory funnel
concentrationThe organic layer was concentrated in vacuo
dissolutionredissolved in DMF (1 mL) for Gilson HPLC separation
additionThe fractions containing the pure product
concentrationwere concentrated in vacuo

Sources & evidence

ORD record: ord-b475803c509743268eacd58242ae1545
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08481733B2

Reaction notes

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