Triethylamine → HCID 67442038, compound

HRID 1800945Notes

Reaction equation

HRID 1800945 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[NH:12][CH:11]([C:16]1[CH:21]=[CH:20]C=C(NC(C(O)=O)(C)C)[CH:17]=1)[C:10]([CH3:30])([CH3:29])[CH2:9]2)=[O:5])[CH3:2].Cl.[CH3:32]N.[CH3:34][N:35]([C:37]([O:41]N1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C([N:60]([CH2:63][CH3:64])[CH2:61][CH3:62])C>ClCCl>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[NH:12][CH:11]([C:16]1[CH:21]=[CH:20][CH:64]=[C:63]([NH:60][C:61]([CH3:62])([C:37](=[O:41])[NH:35][CH3:34])[CH3:32])[CH:17]=1)[C:10]([CH3:30])([CH3:29])[CH2:9]2)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 6364545Methylamine hydrochlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67440493HCID 67440493, compound

Product 1

HCID 67442038HCID 67442038, compoundYield 94.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-[3-(1-carboxy-1-methyl-ethylamino)-phenyl]-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid ethyl ester (410 mg, 1 mmol), methylamine hydrochloride (203 mg, 3 mmol) and o-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (570 mg, 1.5 mmol) in dichloromethane (5 mL) and triethyl-amine (0.5 mL, 3 mmol) was stirred at 25° C. for 12 h. Then the reaction mixture was extracted with dichloromethane (2×100 mL), washed with water, dried over anhydrous sodium sulfate and concentrated in vacuo to afford 3,3-dimethyl-2-[3-(1-methyl-1-methylcarbamoyl-ethylamino)-phenyl]-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid ethyl ester (0.4 g, 94%) as a brown oil which was used for next step without further purification: LC/MS m/e calcd for C25H33N3O3 (M+H)+: 424.56, observed: 424.1.

Workup

  1. extractionThen the reaction mixture was extracted with dichloromethane (2×100 mL)
  2. washwashed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4dde29ecc72b4fcea3aff0fe9b609561
Source dataset
uspto-grants-2013_01
Patent number
US08344137B2

Reaction notes

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