Hydrochloric Acid → 4-chloro-N-(1-methyl-2-oxo-1,2,3,4-tetrahydroquinolin-7-yl)-2-{[(1S*,2S*)-2-pyrrolidin-1-ylcyclohexyl]amino}benzamide

HRID 426006Notes

Reaction equation

HRID 426006 reaction equation
Cl.C(N=C=NCCCN(C)C)C.CN(C1C=CC=CN=1)C.[Cl:22][C:23]1[CH:31]=[CH:30][C:26]([C:27](O)=[O:28])=[C:25]([NH:32][C@H:33]2[CH2:38][CH2:37][CH2:36][CH2:35][C@@H:34]2[N:39]2[CH2:43][CH2:42][CH2:41][CH2:40]2)[CH:24]=1.[NH2:44][C:45]1[CH:54]=[C:53]2[C:48]([CH2:49][CH2:50][C:51](=[O:56])[N:52]2[CH3:55])=[CH:47][CH:46]=1>C(Cl)Cl>[Cl:22][C:23]1[CH:31]=[CH:30][C:26]([C:27]([NH:44][C:45]2[CH:54]=[C:53]3[C:48]([CH2:49][CH2:50][C:51](=[O:56])[N:52]3[CH3:55])=[CH:47][CH:46]=2)=[O:28])=[C:25]([NH:32][C@H:33]2[CH2:38][CH2:37][CH2:36][CH2:35][C@@H:34]2[N:39]2[CH2:40][CH2:41][CH2:42][CH2:43]2)[CH:24]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 218852-DimethylaminopyridineHCID 336993947-amino-1-methyl-3,4-dihydroquinolin-2(1H)-oneHCID 667037374-chloro-2-{[(1S*,2S*)-2-pyrrolidin-1-ylcyclohexyl]amino}benzoic acid

Product 1

HCID 667036994-chloro-N-(1-methyl-2-oxo-1,2,3,4-tetrahydroquinolin-7-yl)-2-{[(1S*,2S*)-2-pyrrolidin-1-ylcyclohexyl]amino}benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Hydrochloride of 1-ethyl-3-[3-(N,N-dimethylamino)propyl]carbodiimide (174 mg) and dimethylaminopyridine (21 mg) were added to a methylene chloride (5 mL) solution of 4-chloro-2-{[(1S*,2S*)-2-pyrrolidin-1-ylcyclohexyl]amino}benzoic acid (220 mg) and 7-amino-1-methyl-3,4-dihydroquinolin-2(1H)-one (100 mg). After stirring the reaction liquid overnight at room temperature, the reaction liquid was concentrated under a reduced pressure. By purifying the residue by silica gel column chromatography (hexane:ethyl acetate, 1:0 to 1:1), 4-chloro-N-(1-methyl-2-oxo-1,2,3,4-tetrahydroquinolin-7-yl)-2-{[(1S*,2S*)-2-pyrrolidin-1-ylcyclohexyl]amino}benzamide was obtained as a pale yellow amorphous. By treating this with 4 M hydrogen chloride/ethyl acetate solution, 4-chloro-N-(1-methyl-2-oxo-1,2,3,4-tetrahydroquinolin-7-yl)-2-{[(1S*,2S*)-2-pyrrolidin-1-ylcyclohexyl]amino}benzamide hydrochloride (212 mg) was obtained as an amorphous.

Workup

  1. customthe reaction liquid overnight at room temperature
  2. customthe reaction liquid
  3. concentrationwas concentrated under a reduced pressure
  4. customBy purifying the residue by silica gel column chromatography (hexane:ethyl acetate, 1:0 to 1:1)

Sources & evidence

ORD record
ord-90288db1859a476595d3fc0a22c4adbc
Source dataset
uspto-grants-2012_01
Patent number
US08106190B2

Reaction notes

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