Ethyl Acetate → N-[6-(2-Acetylaminoethylamino)-2-phenylpyrimidin-4-yl]-2-[4-(4-fluorobenzyl)-piperidin-1-yl]-acetamide

HRID 895473Notes

Reaction equation

HRID 895473 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][NH:7][C:8]1[N:13]=[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:11]=[C:10]([NH:20][C:21](=[O:24])[CH2:22]Cl)[CH:9]=1)(=[O:3])[CH3:2].[F:25][C:26]1[CH:38]=[CH:37][C:29]([CH2:30][CH:31]2[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]2)=[CH:28][CH:27]=1.CCOC(C)=O>CC(O)C>[C:1]([NH:4][CH2:5][CH2:6][NH:7][C:8]1[N:13]=[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:11]=[C:10]([NH:20][C:21](=[O:24])[CH2:22][N:34]2[CH2:35][CH2:36][CH:31]([CH2:30][C:29]3[CH:28]=[CH:27][C:26]([F:25])=[CH:38][CH:37]=3)[CH2:32][CH2:33]2)[CH:9]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 36998414-(4-Fluoro-benzyl)-piperidineHCID 11256532HCID 11256532, compound

Product 1

HCID 22379006N-[6-(2-Acetylaminoethylamino)-2-phenylpyrimidin-4-yl]-2-[4-(4-fluorobenzyl)-piperidin-1-yl]-acetamide

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

This compound was prepared from chloroacetamide 6 (77 mg; 0.221 mmol) and 4-(4-fluorobenzyl)-piperidine (7.9) (47 mg; 0.24 mmol) in a manner analogous to 8.8 yielding a white crystalline solid (80.5 mg; 72%) after silica gel chromatography (12-8:1 EtOAc:i-PrOH). LC (method B) tR=13.1 min; 1H NMR (200 MHz, CDCl3) δ 9.51 (brs, 1H), 8.37 (m, 2H), 7.48 (m, 3H), 7.22 (s, 1H), 7.11 (m, 2H), 6.98 (m, 2H), 6.58 (brs, 1H), 5.45 (brt, J=5.4 Hz, 1H), 3.68 (m, 2H), 3.53 (m, 2H), 3.11 (s, 2H), 2.89 (m, 2H), 2.57 (m, 2H), 2.20 (m, 2H), 1.86 (s, 3H), 1.80-1.30 (m, 5H); ESIMS 505.0 (42) [MH+], 253.1 (100).

Sources & evidence

ORD record
ord-4c5d4ea017324ec08a35dd2356461a71
Source dataset
uspto-grants-2005_07
Patent number
US06916804B2

Reaction notes

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