Hydrochloric Acid → HCID 67441324, compound

HRID 2045652Notes

Reaction equation

HRID 2045652 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:14]=1[NH:13][CH:12]([C:15]1[CH:16]=[C:17]([CH:21]=[CH:22][CH:23]=1)[C:18]([OH:20])=O)[C:11]([CH3:25])([CH3:24])[CH2:10]2)=[O:4].ON1C2C=CC=CC=2N=N1.[CH3:36][N:37]([CH3:46])[CH2:38][CH2:39][CH2:40][N:41]=C=NCC.Cl.CN1CCOCC1.CN1CCC(N)C1>ClCCl>[CH3:25][C:11]1([CH3:24])[CH2:10][C:9]2[C:14](=[C:5]([C:3]([O:2][CH3:1])=[O:4])[CH:6]=[CH:7][CH:8]=2)[NH:13][CH:12]1[C:15]1[CH:23]=[CH:22][CH:21]=[C:17]([C:18](=[O:20])[NH:41][CH:40]2[CH2:39][CH2:38][N:37]([CH3:36])[CH2:46]2)[CH:16]=1

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 189403961-Methylpyrrolidin-3-amineHCID 67442012HCID 67442012, compound

Product 1

HCID 67441324HCID 67441324, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 3-(8-(methoxycarbonyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinolin-2-yl)benzoic acid (63 mg, 0.19 mmol) in dichloromethane (5.0 mL) was added N-hydroxybenzotriazole (37.6 mg, 0.28 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide.hydrochloric acid (106.7 mg, 0.56 mmol), followed by 4-methylmorpholine (56.3 mg, 0.56 mmol) and the resultant mixture was stirred at room temperature for 1 h., then 1-methylpyrrolidin-3-amine (27.9 mg, 0.28 mmol) was added to the flask and the reaction mixture was stirred for an additional 1 h. LC-MS showed the reaction was complete. The reaction was quenched with water and separated. The aqueous layer was extracted with dichloromethane (twice) and the combined organic layers were washed with 5% sodium hydroxide aqueous solution (twice) and water (3 times), dried over anhydrous magnesium sulfate. Removal of the solvent in vacuo gave 76 mg of methyl 3,3-dimethyl-2-(3-(1-methylpyrrolidin-3-ylcarbamoyl)phenyl)-1,2,3,4-tetrahydroquinoline-8-carboxylate as a white solid, which was used in next step without further purification.

Workup

  1. customThe reaction was quenched with water
  2. customseparated
  3. extractionThe aqueous layer was extracted with dichloromethane (twice) and the combined organic layers
  4. washwere washed with 5% sodium hydroxide aqueous solution (twice) and water (3 times)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customRemoval of the solvent in vacuo

Sources & evidence

ORD record
ord-e895ad3747ef430381f1e9b8d2139bfb
Source dataset
uspto-grants-2013_11
Patent number
US08586747B2

Reaction notes

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