Amlodipine → Nicardipine

HRID 1387604

Reaction equation

[CH3:1][CH2:2][O:3][C:4]([C:6]1[CH:11]([C:12]2[CH:13]=[CH:14][CH:15]=[C:16]([N+:18]([O-:20])=[O:19])[CH:17]=2)[C:10]([C:21]([O:23][CH3:24])=[O:22])=[C:9]([CH3:25])[NH:8][C:7]=1[CH3:26])=[O:5].CC1NC(C)=C(C(OCC(C)C)=O)[CH:30]([C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][C:47]=2[N+]([O-])=O)C=1C(OC)=O.CCOC(C1C(C2C=CC=C(Cl)C=2Cl)C(C(OC)=O)=C(C)[NH:62][C:61]=1C)=O.CC1NC(C)=C(C(OC(C)C)=O)C(C2C=CC=C([N+]([O-])=O)C=2)C=1C(OCCOC)=O.CCCOCCOC(C1C(C2C=CC=C([N+]([O-])=O)C=2)C(C(OCCOCCC)=O)=C(C)NC=1C)=O.COC(C1C(C2C=CC=CC=2Cl)C(C(OCC)=O)=C(COCCN)NC=1C)=O.CCOC(C1C(C2C=CC=CC=2C(F)(F)F)C(C(OCC)=O)=C(C)N(CCN2CCOCC2)C=1C)=O.CC1NC(C#N)=C(C(OC)=O)C(C2C=CC=C([N+]([O-])=O)C=2)C=1C(OC(C)C)=O.CC1NC(C)=C(C(OC(C)C)=O)C(C2C3=NON=C3C=CC=2)C=1C(OC)=O>>[CH3:25][C:9]1[NH:8][C:7]([CH3:26])=[C:6]([C:4]([O:3][CH2:2][CH2:1][N:62]([CH2:30][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[CH3:61])=[O:5])[CH:11]([C:12]2[CH:13]=[CH:14][CH:15]=[C:16]([N+:18]([O-:20])=[O:19])[CH:17]=2)[C:10]=1[C:21]([O:23][CH3:24])=[O:22]

Participants

Reactant 9

HCID 4507Nitrendipine

HCID 53699Flordipine

HCID 89767Niludipine

Product 1

HCID 4474Nicardipine

Procedure

Nitrendipine (1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-phyridindicarboxylic acid ethyl methyl ester); Nisoldipine (1,4-dihydro-2,6-dimethyl-4-(2-nitrophenyl)-3,5-pyridinedicarboxylic acid methyl 2-methylpropyl ester); Felodipine (4-(2,3-dichlorophenyl)-1,4dihydro-2,6-dimethyl-3,5-pyridinedicarboxylic acid ethyl methyl ester); Nimodipine (1,4-dihydro-2,6dimethyl-4-(3-nitrophenyl-3,5-pyridinedicarboxylic acid 2-methoxyethyl 1-methylethyl ester); Niludipine; Amlodipine (2-((2-aminoethoxy)methyl)-4-(2-chlorophenyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylic acid 3-ethyl 5-methyl ester); Flordipine; Ryosidine; FR 7534; Nilvadipine (FR 34235, 2-cyano-1,4-dihydro-6-methyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic acid 3-methyl 5-(1-methylethyl) ester); PY 108-068; and Isradipine (PN 200-110, 4-(4-benxofurazanyl)-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylic acid methyl 1-methyl-ethyl ester).

Sources & evidence

ORD record: ord-38bb1e0ddabe4432bff2c94bdb1b4d5e
Source dataset: uspto-grants-2001_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06268377B1

Linked notes

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