Water → 3-Quinolinecarboxamide

HRID 1755939Notes

Reaction equation

HRID 1755939 reaction equation
CO[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]2NC1C=CC(C(NC2CCN(CC3C=CC=CC=3)CC2)=O)=CC=1.FC(F)(F)C1C=C(C[N:48]2CCC(N)CC2)C=CC=1.FC(F)(F)C1C=C(C=CC=1)CCl.O1C2(CCNCC2)OCC1.O>>[N:11]1[C:12]2[C:7](=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:8]=[C:9]([C:13]([NH2:48])=[O:15])[CH:10]=1

Participants

6

Reactant 5

HCID 962WaterHCID 674351,4-Dioxa-8-azaspiro(4.5)decaneHCID 697163-(Trifluoromethyl)benzyl chlorideHCID 128889291-{[3-(Trifluoromethyl)phenyl]methyl}piperidin-4-amine2×HCID 152897728-Methoxy-4-[[4-[[[1-(phenylmethyl)-4-piperidinyl]amino]carbonyl]phenyl]amino]-3-quinolinecarboxylic acid

Product 1

HCID 155611013-Quinolinecarboxamide

Procedure

8-Methoxy-4-[[4-[[[1-(phenylmethyl)-4-piperidinyl]amino]carbonyl]phenyl]amino]-1-[[3-(trifluoromethyl)phenyl]methyl]-4-piperidinyl]-3-quinolinecarboxamide was prepared as a hygroscopic solid (0.46 hydrate) by coupling 8-methoxy-4-[[4-[[[1-(phenylmethyl)-4-piperidinyl]amino]carbonyl]phenyl]amino]-3-quinolinecarboxylic acid and 1-[[3-(trifluoromethyl)phenyl]methyl]-4-piperidinamine as described for Example 17, Step 5. 1-[[3-(trifluoromethyl)phenyl]methyl]-4-piperidinamine can be prepared from 3-(triflouromethyl)benzyl 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 132°-138° C.; 1H NMR (Me2SO-d6, 400 MHz) δ 9.48 (s, 1 H), 8.76 (s, 1 H), 8.39 (d, J=7.6 Hz, 1 H), 7.97 (d, J=7.8 Hz, 1 H), 7.68 (d, J=8.7 Hz, 2 H), 7.10-7.65 (m, 12 H), 6.87 (d, J=8.7 Hz, 2 H), 3.94 (s, 3 H), 3.62-3.80 (m, 1 H), 3.35-3.60 (m, 5 H), 2.6-2.9 (m, 4 H), 1.95 (m, 4 H), 1.3-1.8 (m, 8 H); Karl Fischer, 0.46 moles of H2O.

Sources & evidence

ORD record
ord-76f3cf31eddb421db9861e4517197f1c
Source dataset
uspto-grants-1995_08
Patent number
US05438064

Reaction notes

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