Water → N-[1-[(3-Methoxyphenyl)methyl]-4-piperidinyl]-8-methoxy-4-[[4-[[[1-(phenylmethyl)-4-piperidinyl]amino]carbonyl]phenyl]amino]-3-quinoline-carboxamide

HRID 1755938Notes

Reaction equation

HRID 1755938 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][O:40][C:41]1[CH:42]=[C:43]([CH2:47][N:48]2[CH2:53][CH2:52][CH:51]([NH2:54])[CH2:50][CH2:49]2)[CH:44]=[CH:45][CH:46]=1.COC1C=C(C=CC=1)CCl.O1C2(CCNCC2)OCC1.O>>[CH3:39][O:40][C:41]1[CH:42]=[C:43]([CH2:47][N:48]2[CH2:49][CH2:50][CH:51]([NH:54][C:13]([C:9]3[CH:10]=[N:11][C:12]4[C:7]([C:8]=3[NH:16][C:17]3[CH:18]=[CH:19][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:21][CH:22]=3)=[CH:6][CH:5]=[CH:4][C:3]=4[O:2][CH3:1])=[O:14])[CH2:52][CH2:53]2)[CH:44]=[CH:45][CH:46]=1

Participants

6

Reactant 5

HCID 962WaterHCID 674351,4-Dioxa-8-azaspiro(4.5)decaneHCID 699943-Methoxybenzyl chlorideHCID 126418401-[(3-Methoxyphenyl)methyl]piperidin-4-amine2×HCID 152897728-Methoxy-4-[[4-[[[1-(phenylmethyl)-4-piperidinyl]amino]carbonyl]phenyl]amino]-3-quinolinecarboxylic acid

Product 1

HCID 19918426N-[1-[(3-Methoxyphenyl)methyl]-4-piperidinyl]-8-methoxy-4-[[4-[[[1-(phenylmethyl)-4-piperidinyl]amino]carbonyl]phenyl]amino]-3-quinoline-carboxamide

Procedure

N-[1-[(3-Methoxyphenyl)methyl]-4-piperidinyl]-8-methoxy-4-[[4-[[[1-(phenylmethyl)-4-piperidinyl]amino]carbonyl]phenyl]amino]-3-quinoline-carboxamide was prepared as a hygroscopic solid (0.76 hydrate) by coupling 8-methoxy-4 -[[4-[[[1-(phenylmethyl)-4-piperidinyl]amino]carbonyl]phenyl]amino]-3-quinolinecarboxylic acid and 1-[(3-methoxyphenyl)methyl]-4-piperidinamine as described for Example 17, Step 5. 1-[(3-Methoxyphenyl)methyl]-4-piperidinamine can be prepared from 3-methoxybenzyl chloride and 1,4-dioxa-8-azaspiro[4.5]-decane as described in U.S. Pat. Nos. 3,875,165 and 4,816,464: mp 135°-142° C.; 1H NMR (Me2SO-d6, 400 MHz) δ 9.48 (s, 1 H), 8.76 (s, 1 H), 8.39 (d, J=7.5 Hz, 1 H), 7.98 (d, J=7.7 Hz, 1 H), 7.68 (d, J=8.6 Hz, 2 H), 7.57 (d, J=8.6 Hz, 1H), 7.41 (m, 1H), 7.10-7.35 (m, 8 H), 6.7-6.9 (m, 4 H), 3.94 (s, 3 H), 3.6-3.8 (m, 4 H), 3.2-3.6 (m, 5 H), 2.6-2.9 (m, 4 H), 1.3-2.1 (m, 12 H); Karl Fischer, 0.76 moles of H2O.

Sources & evidence

ORD record
ord-d1b183bd33cd458b8f4222466dd0413d
Source dataset
uspto-grants-1995_08
Patent number
US05438064

Reaction notes

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