4-Methylmorpholine → HCID 86717961, compound

HRID 2275882Notes

Reaction equation

HRID 2275882 reaction equation
[F:1][C:2]1[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[C:3]=1[CH2:4][O:5][C:6]1[C:7]2[N:8]([C:12]([C:16]([OH:18])=O)=[C:13]([CH3:15])[N:14]=2)[CH:9]=[CH:10][CH:11]=1.F[B-](F)(F)F.N1(O[C+](N(C)C)N(C)C)C2C=CC=CC=2N=N1.CN1CCOCC1.[CH3:53][C:54]([NH2:58])([CH3:57])[CH2:55][NH2:56]>CN(C=O)C>[NH2:58][C:54]([CH3:57])([CH3:53])[CH2:55][NH:56][C:16]([C:12]1[N:8]2[CH:9]=[CH:10][CH:11]=[C:6]([O:5][CH2:4][C:3]3[C:19]([F:23])=[CH:20][CH:21]=[CH:22][C:2]=3[F:1])[C:7]2=[N:14][C:13]=1[CH3:15])=[O:18]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 131282-MethylpropylenediamineHCID 867178728-((2,6-Difluorobenzyl)oxy)-2-methylimidazo[1,2-a]pyridine-3-carboxylic acidHCID 178484679HCID 178484679, compound

Product 1

HCID 86717961HCID 86717961, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

100 mg of 8-[(2,6-difluorobenzyl)oxy]-2-methylimidazo[1,2-a]pyridine-3-carboxylic acid (0.31 mmol), 151 mg of (benzotriazol-1-yloxy)bisdimethylaminomethylium fluoroborate (TBTU, 0.47 mmol) and 127 mg of 4-methylmorpholine (1.26 mmol) were initially charged in 2 ml of DMF. 55 mg of 2-methylpropane-1,2-diamine (0.63 mmol) were then added, and the mixture was stirred at RT overnight. The reaction solution was purified by preparative HPLC (RP18 column, mobile phase: acetonitrile/water gradient with addition of 0.1% TFA). The crude product was taken up in ethyl acetate and washed twice with saturated aqueous sodium bicarbonate solution. The aqueous phase was extracted twice with ethyl acetate and the combined organic phases were dried over sodium sulphate. The mixture was then filtered and the filtrate was concentrated and lyophilized. This gave 80 mg of the title compound (66% of theory).

Workup

  1. customThe reaction solution was purified by preparative HPLC (RP18 column, mobile phase: acetonitrile/water gradient with addition of 0.1% TFA)
  2. washwashed twice with saturated aqueous sodium bicarbonate solution
  3. extractionThe aqueous phase was extracted twice with ethyl acetate
  4. dry with materialthe combined organic phases were dried over sodium sulphate
  5. filtrationThe mixture was then filtered
  6. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-6299068ffebd4ee7bc279ab65f21f55b
Source dataset
uspto-grants-2015_09
Patent number
US09126998B2

Reaction notes

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