1-Butanol → HCID 178450730, compound

HRID 2381748Notes

Reaction equation

Cl[C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][NH:8]2)=[C:4]([N:11]2[CH2:16][CH2:15][CH2:14][CH:13]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:12]2)[N:3]=1.[NH2:22][C:23]1[CH:28]=[CH:27][C:26]([N:29]2[CH2:34][CH2:33][N:32]([C:35](=[O:37])[CH3:36])[CH2:31][CH2:30]2)=[CH:25][CH:24]=1.C[Si](Cl)(C)C.[CH2:43](O)[CH2:44]CC>>[C:35]([N:32]1[CH2:31][CH2:30][N:29]([C:26]2[CH:25]=[CH:24][C:23]([NH:22][C:2]3[N:10]=[C:9]4[C:5]([N:6]=[CH:7][NH:8]4)=[C:4]([N:11]4[CH2:16][CH2:15][CH2:14][CH:13]([C:17]([O:19][CH2:20][CH2:21][CH2:43][CH3:44])=[O:18])[CH2:12]4)[N:3]=3)=[CH:28][CH:27]=2)[CH2:34][CH2:33]1)(=[O:37])[CH3:36]

Participants

Reactant 4

HCID 2631-Butanol

HCID 6397Chlorotrimethylsilane

HCID 7362691-[4-(4-Aminophenyl)piperazin-1-yl]ethan-1-one

HCID 178468997HCID 178468997, compound

Product 1

HCID 178450730HCID 178450730, compound

Conditions

Temperature: 135 °C

Procedure

A mixture of ethyl 1-(2-chloro-9H-purin-6-yl)piperidine-3-carboxylate (108 mg, 0.349 mmol), 1-(4-(4-aminophenyl)piperazin-1-yl)ethanone (115 mg, 0.525 mmol) and trimethylsilyl chloride (0.300 mL, 2.37 mmol) in nBuOH (4 mL) was stirred at 135° C. for 20 h. It was concentrated in vacuo. The residue was purified by HPLC to give the titled compound (86 mg). MS 521.4 (M+H); UV 201.8, 272.8 nm.

Workup

concentrationIt was concentrated in vacuo
customThe residue was purified by HPLC

Sources & evidence

ORD record: ord-a9b888a1454e4c9aacf85a7c50b6b0e4
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08258144B2

Reaction notes

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