1-Methyl-4-(methylamino)piperidine → HCID 21850074, compound

HRID 1755937Notes

Reaction equation

HRID 1755937 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](O)=[O:14])=[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.[CH3:39][N:40]1[CH2:45][CH2:44][CH:43]([NH:46]C)[CH2:42][CH2:41]1>>[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]([NH:46][CH:43]1[CH2:44][CH2:45][N:40]([CH3:39])[CH2:41][CH2:42]1)=[O:14])=[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

Participants

3

Reactant 2

HCID 5663231-Methyl-4-(methylamino)piperidineHCID 152897728-Methoxy-4-[[4-[[[1-(phenylmethyl)-4-piperidinyl]amino]carbonyl]phenyl]amino]-3-quinolinecarboxylic acid

Product 1

HCID 21850074HCID 21850074, compound

Procedure

8-Methoxy-N-(1-methyl-4-piperidinyl)-4-[[4-[[[1-(phenylmethyl)-4-piperidinyl]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 commercially available 1-methyl-4-(methylamino)piperidine as described for Example 17, Step 5: mp 230°-232 ° C.; 1H NMR (Me2SO-d6, 400 MHz), 3:1 mixture of amide rotamers, a:b) δ 9.09 (s, 1Ha), 8.84 (s, 1Hb), 8.58 (s, 1Hb), 8.51 (s, 1Ha), 7.98 (d, J=7.9 Hz, 1Ha), 7.93 (d, J=7.9 Hz, 1Hb), 7.78 (d, J=8.7 Hz, 2Hb), 7.71 (d, J=8.7 Hz, 2Ha), 7.65 (d, J=8.3 Hz, 1 H), 7.51 (t, J= 8.5 Hz, 1 H), 7.43 (m, 5Hb), 7.30 (m, 5Ha), 7.24 (d, J=7.5 Hz, 1 H), 6.91 (d, J=8.7 Hz, 2Ha), 6.77 (d, J=8.7 Hz, 2Hb), 3.96 (s, 3 H), 3.74 (m, 2 H), 3.46 (s, 2 H), 3.32 (b, 2 H), 2.80 (d, J=11.6 Hz, 4Ha), 2.69 (s, 3Hb), 2.64 (d, J=12.2 Hz, 4Hb), 2.58 (s, 3Ha), 2.06 (s, 3Ha), 2.00 (t, J=13.9 Hz, 2 H), 1.97 (s, 3Hb), 1.72 (m, 4 H), 1.56-1.59 (m, 4 H).

Sources & evidence

ORD record
ord-49842597d257427a8cd8abb276fdcbd6
Source dataset
uspto-grants-1995_08
Patent number
US05438064

Reaction notes

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