N-Phenethyl-4-piperidinone → N-[1-(2-Phenylethyl)-4-piperidinyl]-8-methoxy-4-[[4-[[[1-(phenylmethyl)-4piperidinyl]amino]carbonyl]phenyl]amino]-3-quinolinecarboxamide

HRID 1755936Notes

Reaction equation

HRID 1755936 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[N:11]=[CH:10][C:9]([C:13]([OH:15])=O)=[C:8]2[NH:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]([NH:25][CH:26]2[CH2:31][CH2:30][N:29]([CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[CH2:28][CH2:27]2)=[O:24])=[CH:19][CH:18]=1.[CH2:39]([N:47]1[CH2:52][CH2:51][CH:50]([NH2:53])[CH2:49][CH2:48]1)[CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1.C(N1CCC(=O)CC1)CC1C=CC=CC=1>>[C:41]1([CH2:40][CH2:39][N:47]2[CH2:52][CH2:51][CH:50]([NH:53][C:13]([C:9]3[CH:10]=[N:11][C:12]4[C:7]([C:8]=3[NH:16][C:17]3[CH:22]=[CH:21][C:20]([C:23]([NH:25][CH:26]5[CH2:31][CH2:30][N:29]([CH2:32][C:33]6[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=6)[CH2:28][CH2:27]5)=[O:24])=[CH:19][CH:18]=3)=[CH:6][CH:5]=[CH:4][C:3]=4[O:2][CH3:1])=[O:15])[CH2:49][CH2:48]2)[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1

Participants

4

Reactant 3

HCID 96437N-Phenethyl-4-piperidinoneHCID 107287881-(2-Phenylethyl)piperidin-4-amine2×HCID 152897728-Methoxy-4-[[4-[[[1-(phenylmethyl)-4-piperidinyl]amino]carbonyl]phenyl]amino]-3-quinolinecarboxylic acid

Product 1

HCID 21850076N-[1-(2-Phenylethyl)-4-piperidinyl]-8-methoxy-4-[[4-[[[1-(phenylmethyl)-4piperidinyl]amino]carbonyl]phenyl]amino]-3-quinolinecarboxamide

Procedure

N-[1-(2-Phenylethyl)-4-piperidinyl]-8-methoxy-4-[[4-[[[1-(phenylmethyl)- 4piperidinyl]amino]carbonyl]phenyl]amino]-3-quinolinecarboxamide was prepared by coupling 8-methoxy-4-[[4-[[[1-(phenylmethyl)-4-piperidinyl]amino]carbonyl]phenyl]amino]-3-quinolinecarboxylic acid and 1-phenethyl-4-aminopiperidine as described for Example 17, Step 5. 1-phenethyl-4-aminopiperidine can be prepared from 1-phenethyl-4-piperidone as described in U.S. Pat. No. 3,875,165: mp 216°-220 ° C.; 1H NMR (Me2SO-d6, 400 MHz) δ 9.51 (s, 1 H), 8.79 (s, 1 H), 8.40 (d, 5=7.7 Hz, 1 H), 8.00 (d, J=7.7 Hz, 1 H), 7.71 (d, J=8.7 Hz, 2 H), 7.57 (d, J=8.5 Hz, 1 H), 7.41 (m, 1 H), 7.10- 7.35 (m, 11 H), 6.88 (d, J=8.7 Hz, 2 H), 3.93 (s, 3 H), 3.7-3.8 (m, 1 H), 3.4-3.6 (m, 3 H), 2.6-2.9 (m, 6 H), 2.4-2.5 (m, 2 H), 1.85-2.10 (m, 4 H, 1.7-1.8 (m, 2 H), 1.5-1.7 (m, 4 H), 1.3-1.5 (m, 2 H).

Sources & evidence

ORD record
ord-4664432935574fc59aa522b572312b59
Source dataset
uspto-grants-1995_08
Patent number
US05438064

Reaction notes

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