Oxalyl chloride → Pyrimidine-5-carbonyl chloride

HRID 553005Notes

Reaction equation

HRID 553005 reaction equation
ClC1C=CC([N:8]([CH2:30][CH3:31])[C:9]([C@@H:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]([C:21]([C:23]3[CH:24]=[N:25][CH:26]=[N:27][CH:28]=3)=[O:22])[C@@H:13]([CH3:29])[CH2:12]2)=[O:10])=CC=1.FC(F)(F)[C:34]1[CH:42]=[CH:41][C:37](C([Cl:40])=O)=[CH:36][CH:35]=1.N1C=C(C(O)=O)C=NC=1.C(Cl)(=O)C([Cl:57])=O>C(Cl)Cl.CN(C)C=O>[N:25]1[CH:24]=[C:23]([C:21]([Cl:40])=[O:22])[CH:28]=[N:27][CH:26]=1.[Cl:57][C:34]1[CH:42]=[CH:41][C:37]([CH2:31][CH2:30][NH:8][C:9]([CH:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]([C:21]([C:23]3[CH:24]=[N:25][CH:26]=[N:27][CH:28]=3)=[O:22])[CH:13]([CH3:29])[CH2:12]2)=[O:10])=[CH:36][CH:35]=1

Participants

8

Reactant 4

HCID 65578Oxalyl chlorideHCID 676074-(Trifluoromethyl)benzoyl chlorideHCID 78346Pyrimidine-5-carboxylic acidHCID 58732839(+/-)-trans-2-Methyl-1-(pyrimidine-5-carbonyl)-1,2,3,4-tetrahydro-quinoline-4-carboxylic acid (4-chloro-phenyl)-ethyl-amide

Product 2

HCID 15839553Pyrimidine-5-carbonyl chlorideHCID 866085982-Methyl-1-(pyrimidine-5-carbonyl)-1,2,3,4-tetrahydro-quinoline-4-carboxylic acid (4-chloro-phenyl)ethyl-amide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

(±)-trans-2-Methyl-1-(pyrimidine-5-carbonyl)-1,2,3,4-tetrahydro-quinoline-4-carboxylic acid (4-chloro-phenyl)-ethyl-amide was made following general procedure A, substituting pyrimidine-5-carbonyl chloride for 4-trifluoromethyl-benzoyl chloride. Pyrimidine-5-carbonyl chloride was prepared by reaction of pyrimidine-5-carboxylic acid with oxalyl chloride and dimethylformamide in methylene chloride. The crude 2-methyl-1-(pyrimidine-5-carbonyl)-1,2,3,4-tetrahydro-quinoline-4-carboxylic acid (4-chloro-phenyl)ethyl-amide was isolated as a mixture of cis and trans isomers. Purification by silica gel chromatography (2% methanol/methylene chloride) yielded (±)-trans-2-methyl-1-(pyrimidine-5-carbonyl)-1,2,3,4-tetrahydro-quinoline-4-carboxylic acid (4-chloro-phenyl)-ethyl-amide (44%). 1H-NMR (CDCl3) δ: 1.02-1.18 (m, 6H), 1.65-1.75 (m, 1H), 2.50-2.60 (m, 1H), 3.60-3.70 (m, 1H), 3.80 (q, 2H), 4.98-5.10 (m, 1H), 6.40 (d, 1H), 6.70 (d, 1H), 6.90-7.00 (m, 2H), 7.20 (d, 2H), 7.50 (d, 2H), 8.85 (s, 2H), 9.15 (s, 1H). MS m/z: 435/437 (M+1).

Sources & evidence

ORD record
ord-6b3a8cd735564d28a7d128cdfa8ff69c
Source dataset
uspto-grants-2011_05
Patent number
US07951950B2

Reaction notes

Loading…