Acrylic Acid → HCID 118390075, compound

HRID 1477949Notes

Reaction equation

HRID 1477949 reaction equation
[CH3:1][N:2]([CH:16]1[C:20]2([CH2:24][CH2:23][CH2:22][CH2:21]2)[CH2:19][NH:18][CH2:17]1)[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](O)(=[O:28])[CH:26]=[CH2:27].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(CC)CC>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:16]1[C:20]2([CH2:24][CH2:23][CH2:22][CH2:21]2)[CH2:19][N:18]([C:25](=[O:28])[CH:26]=[CH2:27])[CH2:17]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 118390075HCID 118390075, compoundYield 21.1%

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, 0.31 mmol) in DCM (8.0 mL) was added acrylic acid (55 mg, 0.76 mmol), HATU (0.14 g, 0.37 mmol) and Et3N (62 mg, 0.61 mmol). The mixture was stirred at room temperature for 4 h, then diluted with DCM (50 mL), and washed with water (20 mL) followed by brine (20 mL), dried over anhydrous Na2SO4, then filtered and concentrated in vacuo. The residue was purified by preparative-TLC (DCM/MeOH (v/v)=12/1) to give the product as a light yellow solid (25 mg, 21%).

Workup

  1. washwashed with water (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)=12/1)

Sources & evidence

ORD record
ord-7f94803799d1449a8c946bea6e0a57b6
Source dataset
uspto-grants-2016_08
Patent number
US09403801B2

Reaction notes

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