4-Methylmorpholine → HCID 86717964, compound

HRID 2275886Notes

Reaction equation

HRID 2275886 reaction equation
[CH3:1][C:2]1([CH3:11])[CH2:7][CH:6]([NH2:8])[CH2:5][C:4]([CH3:10])([CH3:9])[NH:3]1.[F:12][C:13]1[CH:33]=[CH:32][CH:31]=[C:30]([F:34])[C:14]=1[CH2:15][O:16][C:17]1[C:18]2[N:19]([C:23]([C:27](O)=[O:28])=[C:24]([CH3:26])[N:25]=2)[CH:20]=[CH:21][CH:22]=1.F[B-](F)(F)F.N1(O[C+](N(C)C)N(C)C)C2C=CC=CC=2N=N1.CN1CCOCC1>CN(C=O)C>[F:12][C:13]1[CH:33]=[CH:32][CH:31]=[C:30]([F:34])[C:14]=1[CH2:15][O:16][C:17]1[C:18]2[N:19]([C:23]([C:27]([NH:8][CH:6]3[CH2:5][C:4]([CH3:10])([CH3:9])[NH:3][C:2]([CH3:11])([CH3:1])[CH2:7]3)=[O:28])=[C:24]([CH3:26])[N:25]=2)[CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 375244-Amino-2,2,6,6-tetramethylpiperidineHCID 867178728-((2,6-Difluorobenzyl)oxy)-2-methylimidazo[1,2-a]pyridine-3-carboxylic acidHCID 178484679HCID 178484679, compound

Product 1

HCID 86717964HCID 86717964, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

18.8 mg (0.12 mmol) of 2,2,6,6-tetramethylpiperidine-4-amine were initially charged, and 32 mg (0.10 mmol) of 8-[(2,6-difluorobenzyl)oxy]-2-methylimidazo[1,2-a]pyridine-3-carboxylic acid in 0.4 ml of DMF and 42 mg (0.13 mmol) of (benzotriazol-1-yloxy)bisdimethylaminomethylium fluoroborate (TBTU) in 0.2 ml of DMF were added. 20 mg (0.20 mmol) of 4-methylmorpholine were then added, and the reaction was stirred at RT overnight. The mixture was then filtered off and the filtrate was purified by preparative LC-MS (Method 12). The product-containing fractions were concentrated under reduced pressure. This gave 27 mg (59% of theory) of the target product.

Workup

  1. filtrationThe mixture was then filtered off
  2. customthe filtrate was purified by preparative LC-MS (Method 12)
  3. concentrationThe product-containing fractions were concentrated under reduced pressure

Sources & evidence

ORD record
ord-bf2ece3718354579a31a382cb38fc3bc
Source dataset
uspto-grants-2015_09
Patent number
US09126998B2

Reaction notes

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