Acrylic Acid → HCID 118389999, compound

HRID 1477991Notes

Reaction equation

HRID 1477991 reaction equation
[CH3:1][N:2](C1C2(CCCC2)CNC1)[C:3]1[CH:8]=[CH:7][N:6]=[C:5]([NH:9][C:10]2[CH:11]=[N:12][N:13]([CH3:15])[CH:14]=2)[N:4]=1.[C:25]([OH:29])(=O)[CH:26]=[CH2:27].CN(C(ON1N=N[C:40]2[CH:41]=[CH:42][CH:43]=N[C:39]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CC[N:56]([CH2:59][CH3:60])[CH2:57][CH3:58]>C(Cl)Cl>[CH3:1][N:2]([C:3]1[CH:8]=[CH:7][N:6]=[C:5]([NH:9][C:10]2[CH:11]=[N:12][N:13]([CH3:15])[CH:14]=2)[N:4]=1)[CH:41]1[CH2:42][CH2:43][C:58]2([CH2:57][N:56]([C:25](=[O:29])[CH:26]=[CH2:27])[CH2:59][CH2:60]2)[CH2:39][CH2:40]1

Participants

6

Reactant 4

HCID 6581Acrylic AcidHCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 118410921HCID 118410921, compound

Product 1

HCID 118389999HCID 118389999, compoundYield 23.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of N4-methyl-N2-(1-methyl-1H-pyrazol-4-yl)-N4-(2-azaspiro[4.4]nonan-4-yl)pyrimidine-2,4-diamine (0.10 g, 0.29 mmol) in DCM (10.0 mL) were added acrylic acid (21 mg, 0.29 mmol), HATU (0.13 g, 0.35 mmol) and Et3N (59 mg, 0.59 mmol). The mixture was stirred at rt for 1.5 h, and then diluted with DCM (30 mL), washed with brine (20 mL), dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by preparative-TLC (DCM/MeOH (v/v)=20/1) to give the title compound as a light yellow solid (27 mg, 21%).

Workup

  1. washwashed with brine (20 mL)
  2. dry with materialdried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by preparative-TLC (DCM/MeOH (v/v)=20/1)

Sources & evidence

ORD record
ord-1b31e77857714f1ba41518319b20c2bb
Source dataset
uspto-grants-2016_08
Patent number
US09403801B2

Reaction notes

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