Benzenamine, 4-(4-morpholinyl)- → 6-Ethoxy-8-(4-methyl-piperazin-1-yl)-4-oxo-4H-chromene-2-carboxylic Acid (4-(4-propionyl-piperazin-1-yl)-phenyl]-amide

HRID 1181988Notes

Reaction equation

HRID 1181988 reaction equation
C(OC1C=CC2SC([NH:12][C:13]([C:15]3[O:16][C:17]4[C:22]([C:23](=[O:25])[CH:24]=3)=[CH:21][CH:20]=[CH:19][C:18]=4[N:26]3[CH2:31][CH2:30][N:29]([CH3:32])[CH2:28][CH2:27]3)=[O:14])=NC=2C=1)C.N[C:35]1[CH:40]=[CH:39][C:38]([N:41]2[CH2:46][CH2:45][N:44]([C:47](=[O:50])[CH2:48][CH3:49])[CH2:43][CH2:42]2)=[CH:37][CH:36]=1.[O:51]1CCN(C2C=CC(N)=CC=2)[CH2:53][CH2:52]1>>[C:47]([N:44]1[CH2:45][CH2:46][N:41]([C:38]2[CH:39]=[CH:40][C:35]([NH:12][C:13]([C:15]3[O:16][C:17]4[C:22]([C:23](=[O:25])[CH:24]=3)=[CH:21][C:20]([O:51][CH2:52][CH3:53])=[CH:19][C:18]=4[N:26]3[CH2:27][CH2:28][N:29]([CH3:32])[CH2:30][CH2:31]3)=[O:14])=[CH:36][CH:37]=2)[CH2:42][CH2:43]1)(=[O:50])[CH2:48][CH3:49]

Participants

4

Reactant 3

HCID 75655Benzenamine, 4-(4-morpholinyl)-HCID 9347841-(4-(4-Aminophenyl)piperazin-1-yl)propan-1-oneHCID 235333708-(4-Methyl-piperazin-1-yl)-4-oxo-4H-chromene-2-carboxylic acid (5-ethoxy-benzothiazol-2-yl)-amide

Product 1

HCID 235332996-Ethoxy-8-(4-methyl-piperazin-1-yl)-4-oxo-4H-chromene-2-carboxylic Acid (4-(4-propionyl-piperazin-1-yl)-phenyl]-amideYield 12%

Procedure

This compound was prepared from 250 mg (0.68 mmol, 1.0 equiv.) of 6-Ethoxy-8-(4-methyl-piperazin-1-yl)-4-oxo-4H-chromene-2-carbonyl chloride (Reference Example 23) and 175 mg (0.748 mmol, 1.1 equiv.) of 1-[4-(4-Amino-phenyl)-piperazin-1-yl]-propan-1-one by an analogous procedure to that used to prepare the 4-morpholino aniline derivative, to give 45 mg (12%) of the desired product as a yellow solid.

Sources & evidence

ORD record
ord-b84f9c6f773b4bd5955b0fd2203ee0b3
Source dataset
uspto-grants-2007_10
Patent number
US07285662B2

Reaction notes

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