HCID 58515929, compound → HCID 178473887, compound

HRID 717841Notes

Reaction equation

[C:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[N:15]3[CH:16]=[N:17][CH:18]=[C:14]3[C:13]([Cl:19])=[CH:12][C:11]=2[CH:20]([NH2:22])[CH3:21])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].Br[C:24]1[N:32]=[CH:31][N:30]=[C:29]2[C:25]=1[N:26]=[CH:27][NH:28]2>C(O)C>[C:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[N:15]3[CH:16]=[N:17][CH:18]=[C:14]3[C:13]([Cl:19])=[CH:12][C:11]=2[CH:20]([NH:22][C:24]2[N:32]=[CH:31][N:30]=[C:29]3[C:25]=2[N:26]=[CH:27][NH:28]3)[CH3:21])[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 1-[5-(4-acetylpiperazin-1-yl)-8-chloroimidazo[1,5-a]pyridin-6-yl]ethanamine (11.2 mg, 0.035 mmol), 6-bromo-9H-purine (14 mg, 0.070 mmol) and IV, N-diisopropylethylamine (18 μL, 0.10 mmol) in ethanol (0.93 mL) was heated to 110° C. overnight. Purification by preparative LCMS (pH 10) gave the desired compound (6.7 mg, 44%). LCMS calculated for C20H23ClN9O (M+H)+: m/z=440.2. found: 439.9. 1H NMR (300 MHz, DMSO-d6): δ 8.52 (s, 1H), 8.17 (m, 3H), 7.42 (s, 1H), 7.37 (s, 1H), 5.90 (s, 1H), 3.80 (m, 2H), 3.65 (m, 2H), 3.50 (m, 1H), 3.40 (m, 2H), 3.20 (m, 2H), 2.09 (s, 3H), 1.52, (m, 3H).

Workup

customPurification by preparative LCMS (pH 10)

Sources & evidence

ORD record: ord-903488484d0740e598f24a02288398bf
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193721B2

Reaction notes

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