4-Methylmorpholine → rac-tert-Butyl 2-{[({8-[(2,6-difluorobenzyl)oxy]-2-methylimidazo[1,2-a]pyridin-3-yl}carbonyl)-amino]methyl}-3,4-dihydroquinoline-1(2H)-carboxylate

HRID 2275856Notes

Reaction equation

HRID 2275856 reaction equation
CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CN1CCOCC1.[F:30][C:31]1[CH:51]=[CH:50][CH:49]=[C:48]([F:52])[C:32]=1[CH2:33][O:34][C:35]1[C:36]2[N:37]([C:41]([C:45](O)=[O:46])=[C:42]([CH3:44])[N:43]=2)[CH:38]=[CH:39][CH:40]=1.Cl.[NH2:54][CH2:55][CH:56]1[CH2:65][CH2:64][C:63]2[C:58](=[CH:59][CH:60]=[CH:61][CH:62]=2)[N:57]1[C:66]([O:68][C:69]([CH3:72])([CH3:71])[CH3:70])=[O:67]>CN(C=O)C.O>[F:30][C:31]1[CH:51]=[CH:50][CH:49]=[C:48]([F:52])[C:32]=1[CH2:33][O:34][C:35]1[C:36]2[N:37]([C:41]([C:45]([NH:54][CH2:55][CH:56]3[CH2:65][CH2:64][C:63]4[C:58](=[CH:59][CH:60]=[CH:61][CH:62]=4)[N:57]3[C:66]([O:68][C:69]([CH3:72])([CH3:71])[CH3:70])=[O:67])=[O:46])=[C:42]([CH3:44])[N:43]=2)[CH:38]=[CH:39][CH:40]=1

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 46738139Tert-butyl 2-(aminomethyl)-3,4-dihydroquinoline-1(2h)-carboxylate hydrochlorideHCID 867178728-((2,6-Difluorobenzyl)oxy)-2-methylimidazo[1,2-a]pyridine-3-carboxylic acid

Product 1

HCID 90114381rac-tert-Butyl 2-{[({8-[(2,6-difluorobenzyl)oxy]-2-methylimidazo[1,2-a]pyridin-3-yl}carbonyl)-amino]methyl}-3,4-dihydroquinoline-1(2H)-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

145 mg (0.45 mmol) of TBTU and 0.2 ml (1.89 mmol) of 4-methylmorpholine were added to 120 mg (0.38 mmol) of 8-[(2,6-difluorobenzyl)oxy]-2-methylimidazo[1,2-a]pyridine-3-carboxylic acid Example 3A in 2.4 ml of DMF, and the mixture was stirred at RT for 10 min. 124 mg (0.42 mmol) of rac-tert-butyl 2-(aminomethyl)-3,4-dihydroquinoline-1(2H)-carboxylate hydrochloride were added and the reaction mixture was stirred at RT overnight. Water was added, and the reaction mixture was stirred at RT for 30 min. The precipitated solid was filtered off, washed with water and dried under high vacuum. This gave 190 mg (90% of theory; purity 100%) of the title compound.

Workup

  1. stirringthe reaction mixture was stirred at RT overnight
  2. stirringthe reaction mixture was stirred at RT for 30 min
  3. filtrationThe precipitated solid was filtered off
  4. washwashed with water
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-53a8ff878d224aafa3fd646e1d94a583
Source dataset
uspto-grants-2015_09
Patent number
US09126998B2

Reaction notes

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