Methylamine → HCID 67440709, compound

HRID 1801058Notes

Reaction equation

HRID 1801058 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([Cl:30])[CH:8]=[C:9]2[C:14]=1[NH:13][CH:12]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([NH:21][C:22]([C:25](O)=[O:26])([CH3:24])[CH3:23])[CH:16]=1)[C:11]([CH3:29])([CH3:28])[CH2:10]2)=[O:4].Cl.[CH3:32][N:33](C)CCCN=C=NCC.CN.C(N(CC)CC)C>CN(C)C1C=CN=CC=1.O1CCCC1.ClCCl>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([Cl:30])[CH:8]=[C:9]2[C:14]=1[NH:13][CH:12]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([NH:21][C:22]([CH3:24])([C:25](=[O:26])[NH:33][CH3:32])[CH3:23])[CH:16]=1)[C:11]([CH3:28])([CH3:29])[CH2:10]2)=[O:4]

Participants

8

Reactant 4

HCID 6329MethylamineHCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 53491902HCID 53491902, compound

Product 1

HCID 67440709HCID 67440709, compoundYield 100%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-[3-(1-carboxy-1-methyl-ethylamino)-phenyl]-6-chloro-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-8-carboxylic acid methyl ester (73 mg, 0.17 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (65 mg, 0.34 mmol), 4-dimethylaminopyridine (41.5 mg, 0.34 mmol), methaneamine (0.26 mL, 0.52 mmol) in tetrahydrofuran and triethylamine (34 mg, 0.34 mmol) in dichloromethane (10 mL) was stirred for 48 hours. Removal of the solvent to afford the crude product 6-chloro-3,3-dimethyl-2-[3-(1-methyl-1-methylcarbamoyl-ethylamino)-phenyl]-1,2,3,4-tetrahydro-quinoline-8-carboxylic acid methyl ester (75 mg, 100%) which was used in next step without purification: LC/MS m/e calcd for C24H30ClN3O3 (M+H)+: 444.98, observed: 444.1.

Workup

  1. customRemoval of the solvent

Sources & evidence

ORD record
ord-118176ff30eb4ea887d80bbcfa9fee6b
Source dataset
uspto-grants-2013_01
Patent number
US08344137B2

Reaction notes

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