4-Methylmorpholine → HCID 117864657, compound

HRID 1486339Notes

Reaction equation

HRID 1486339 reaction equation
[F:1][C:2]1[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[C:3]=1[CH2:4][O:5][C:6]1[N:11]2[N:12]=[C:13]([CH3:18])[C:14]([C:15]([OH:17])=O)=[C:10]2[CH:9]=[C:8]([CH3:19])[CH:7]=1.[NH2:25][CH:26]([C:29]1[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=1)[C:27]#[N:28].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN1CCOCC1>CN(C=O)C>[Cl:35][C:32]1[CH:31]=[CH:30][C:29]([CH:26]([C:27]#[N:28])[NH:25][C:15]([C:14]2[C:13]([CH3:18])=[N:12][N:11]3[C:6]([O:5][CH2:4][C:3]4[C:20]([F:24])=[CH:21][CH:22]=[CH:23][C:2]=4[F:1])=[CH:7][C:8]([CH3:19])=[CH:9][C:10]=23)=[O:17])=[CH:34][CH:33]=1

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 11309731HCID 11309731, compoundHCID 117859510HCID 117859510, compound

Product 1

HCID 117864657HCID 117864657, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

33 mg (0.10 mmol) of 7-[(2,6-difluorobenzyl)oxy]-2,5-dimethylpyrazolo[1,5-a]pyridine-3-carboxylic acid from Example 4A were initially charged in a 96-well deep well multititre plate. A solution of 17 mg (0.10 mmol) of rac-amino(4-chlorophenyl)acetonitrile in 0.4 ml of DMF and a solution of 45.6 mg (0.12 mol) of HATU in 0.4 ml of DMF were added successively. After adding 20.2 mg (0.20 mmol) of 4-methylmorpholine, the mixture was shaken at RT overnight. Then the mixture was filtered and the target compound was isolated from the filtrate by preparative LC-MS (Method 9). The product-containing fractions were concentrated under reduced pressure using a centrifugal dryer. The residue of each product fraction was dissolved in 0.6 ml of DMSO. These were combined and finally freed of the solvent in a centrifugal dryer. 0.7 mg (1.5% of theory) were obtained.

Workup

  1. filtrationThen the mixture was filtered
  2. customthe target compound was isolated from the filtrate by preparative LC-MS (Method 9)
  3. concentrationThe product-containing fractions were concentrated under reduced pressure
  4. dissolutionThe residue of each product fraction was dissolved in 0.6 ml of DMSO
  5. custom0.7 mg (1.5% of theory) were obtained

Sources & evidence

ORD record
ord-c346b55c191449aab1a0f600cb23a801
Source dataset
uspto-grants-2016_08
Patent number
US09422285B2

Reaction notes

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