Diisopropylethylamine → N-(3-isopropylphenyl)-4-methyl-3-[2-(methylthio)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl]benzamide

HRID 338745Notes

Reaction equation

HRID 338745 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][C:3]=1[N:11]1[CH2:25][CH2:24][C:14]2[N:15]=[C:16]([S:19](=O)(=O)NC)[N:17]=[CH:18][C:13]=2[CH2:12]1.[CH:26]([C:29]1[CH:30]=[C:31]([CH:33]=[CH:34][CH:35]=1)[NH2:32])([CH3:28])[CH3:27].[CH3:36]CN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[CH:26]([C:29]1[CH:30]=[C:31]([NH:32][C:6](=[O:7])[C:5]2[CH:9]=[CH:10][C:2]([CH3:1])=[C:3]([N:11]3[CH2:25][CH2:24][C:14]4[N:15]=[C:16]([S:19][CH3:36])[N:17]=[CH:18][C:13]=4[CH2:12]3)[CH:4]=2)[CH:33]=[CH:34][CH:35]=1)([CH3:28])[CH3:27]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 4586793-IsopropylanilineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 866958614-Methyl-3-[2-(methylsulfamyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-6-yl]benzoic acid

Product 1

HCID 71735693N-(3-isopropylphenyl)-4-methyl-3-[2-(methylthio)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl]benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-methyl-3-[2-(methylsulfamyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-6-yl]benzoic acid (67 mg, 0.212 mmol), 3-isopropylaniline (0.03 ml, 0.212 mmol) and N,N′-diisopropylethylamine (0.18 ml, 1.06 mmol) in DMF (1.0 ml) was treated with HATU (89 mg, 0.233 mmol). After stirring at room temperature for 1.5 hours, the reaction mixture was partitioned between water and ethyl acetate. The organic phase was washed with sat'd NaCl(aq.), dried (MgSO4), filtered, and concentrated. Trituration of the residue with cold MeOH yielded the title compound as a white, crystalline solid (50 mg, 55%).

Workup

  1. customthe reaction mixture was partitioned between water and ethyl acetate
  2. washThe organic phase was washed with sat'd NaCl(aq.)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7a6b0a671c584829a1731a728b109ee6
Source dataset
uspto-grants-2014_11
Patent number
US08889870B2

Reaction notes

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