1,4-Dioxa-8-azaspiro(4.5)decane → 8-Methoxy-4-[[4-[[[1-(phenylmethyl)-4-piperidinyl]amino]carbonyl]phenyl]amino]-3-quinoline-carbox-amide

HRID 1755929

반응식

HRID 1755929 반응식
[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.CC(C1C=CC(C[N:50]2CCC(N)CC2)=CC=1)(C)C.ClC1C=C2C(C(NC3C=CC(C(NC4CCN(CC5C=CC=CC=5)CC4)=O)=CC=3)=C(C(O)=O)C=N2)=CC=1.C(OC(C1C(=O)C2C(=C(OC)C=CC=2)NC=1)=O)C.C(C1C=CC(CBr)=CC=1)(C)(C)C.O1C2(CCNCC2)OCC1>O>[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]([NH2:50])=[O:15])=[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

참가 물질

8

반응물 6

HCID 674351,4-Dioxa-8-azaspiro(4.5)decaneHCID 878361-(Bromomethyl)-4-(1,1-dimethylethyl)benzeneHCID 304556Ethyl 4-hydroxy-8-methoxyquinoline-3-carboxylate2회HCID 152897637-Chloro-4-[[4-[[[1-(phenylmethyl)-4-piperidinyl]amino]carbonyl]phenyl]amino]-3-quinolinecarboxylic acidHCID 152897711-[[4-(1,1-Dimethylethyl)phenyl]methyl]-4-piperidinamine2회HCID 152897728-Methoxy-4-[[4-[[[1-(phenylmethyl)-4-piperidinyl]amino]carbonyl]phenyl]amino]-3-quinolinecarboxylic acid2회

생성물 1

HCID 867488398-Methoxy-4-[[4-[[[1-(phenylmethyl)-4-piperidinyl]amino]carbonyl]phenyl]amino]-3-quinoline-carbox-amide

시약·촉매·용매 1

HCID 962Water용매

실험 절차

N-[1-[4-(1,1-Dimethylethyl)pheny]]methyl]-4-piperidiny]]-8-methoxy-4-[[4-[[[1-(phenylmethyl)-4-piperidinyl]amino]carbonyl]phenyl]amino]-3-quinoline-carbox-amide was prepared as a hygroscopic solid (0.2 hydrate) by coupling 8-methoxy-4-[[4-[[[1-(phenylmethyl)-4-piperidinyl]amino]carbonyl]phenyl]amino]-3-quinoline-carboxylic acid and 1-[[4-(1,1-dimethylethyl)phenyl]methyl]-4piperidinamine as described for Example 17, Step 5. 8-Methoxy-4-[[4-[[[1-(phenylmethyl)-4-piperi-dinyl]amino]carbonyl]phenyl]amino]-3-quinolinecarboxylic acid can be prepared as described for 7-chloro-4-[[4-[[[1-(phenylmethyl)-4-piperidinyl]amino]carbonyl]phenyl]amino]-3-quinolinecarboxylic acid in Example 17, Steps 1-4, by starting with 1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid ethyl ester in Step 1. 1,4-Dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid ethyl ester can be prepared as described by C. C. Price et al in J. Am. Chem. Soc., 68, 1204 (1946). 1-[[4-(1,1-Dimethylethyl)phenyl]methyl]-4-piperidinamine can be prepared from 4-(tert-butyl)benzyl bromide and 1,4-dioxa-8-azaspiro[4.5]-decane as described in U.S. Pat. Nos. 3,875,165 and 4,816,464: mp 154°-162 ° C.; 1H NMR (Me2SO-d6, 400 MHz) δ9.47 (s, 1 H), 8.76 (s, 1 H), 8.39 (d, J=7.5 Hz, 1 H), 7.99 (d, J=7.6 Hz, 1 H), 7.68 (d, J=8.7 Hz, 2 H), 7.57 (d, jr=8.3 Hz, 1 H), 7.41 (m, 1 H), 7.10-7.36 (m, 10 H), 6.87 (d, J=8.7 Hz, 2 H), 3.95 (s, 3 H), 3.7 (m, 1 H), 3.2-3.6 (m, 5 H), 2.6-2.9 (m, 4 H), 1.8-2.1 (m, 4 H), 1.3-1.8 (m, 3 H), 1.24 (s, 9 H); Karl Fisher, 0.47% H2O.

출처 및 근거

ORD 기록
ord-53efd16c64fa47c09e988c323feba4e9
출처 데이터셋
uspto-grants-1995_08
특허 번호
US05438064

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