4-Phenylpiperidine → HCID 49779771, compound

HRID 449428Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[CH:17]=[C:16]3[C:11]([CH2:12][CH2:13][N:14]([C:18](OC4C=CC([N+]([O-])=O)=CC=4)=[O:19])[CH2:15]3)=[CH:10][CH:9]=2)[CH:5]=[C:4]([N:30]2[CH2:35][CH2:34][N:33]([CH3:36])[CH2:32][CH2:31]2)[N:3]=1.[C:37]1([CH:43]2[CH2:48][CH2:47][NH:46][CH2:45][CH2:44]2)[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.C(N(CC)C(C)C)(C)C>CN1CCCC1=O>[CH3:36][N:33]1[CH2:34][CH2:35][N:30]([C:4]2[CH:5]=[C:6]([C:8]3[CH:17]=[C:12]4[C:11]([CH2:16][CH2:15][N:14]([C:18]([N:46]5[CH2:47][CH2:48][CH:43]([C:37]6[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=6)[CH2:44][CH2:45]5)=[O:19])[CH2:13]4)=[CH:10][CH:9]=3)[N:7]=[C:2]([NH2:1])[N:3]=2)[CH2:31][CH2:32]1

Participants

Conditions

Temperature: 110 °C

Procedure

4-Nitrophenyl 7-[2-amino-6-(4-methylpiperazin-1-yl)pyrimidin-4-yl]-3,4-dihydroisoquinoline-2(1H)-carboxylate (10 mg, 0.02 mmol) was added to a mixture of 4-phenylpiperidine (4.9 mg, 0.031 mmol) (Aldrich, Cat. #639869) and N,N-diisopropylethylamine (11 uL, 0.061 mmol) in N-methylpyrrolidinone (0.5 mL). The reaction mixture was stirred at 110° C. for 5 h. The mixture was purified by RP-LCMS (pH=10) to afford the desired product. Analytic LCMS (M+H)+: m/z=512.3.

Workup

customThe mixture was purified by RP-LCMS (pH=10)

Sources & evidence

ORD record: ord-3a0158a34da4421aa25d8c3a0b0619f4
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08481732B2

Reaction notes

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