4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride → HCID 59200002, compound

HRID 2382073Notes

Reaction equation

HRID 2382073 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[N:13]=[C:12]([CH3:14])[C:11]([C:15]([OH:17])=O)=[CH:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1.[CH3:18][O:19][C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[N:25]([NH2:29])[C:24]([CH3:30])=[CH:23]2.C[N+]1(C2N=C(OC)N=C(OC)N=2)CCOCC1.[Cl-]>CN(C=O)C>[CH3:18][O:19][C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[N:25]([NH:29][C:15]([C:11]1[C:12]([CH3:14])=[N:13][C:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=3)=[N:9][CH:10]=1)=[O:17])[C:24]([CH3:30])=[CH:23]2

Participants

5

Reactant 3

HCID 27340594-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chlorideHCID 617025872-(3-Fluorophenyl)-4-methylpyrimidine-5-carboxylic acidHCID 68555193HCID 68555193, compound

Product 1

HCID 59200002HCID 59200002, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 2-(3-fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (719 mg, 3.1 mmol) and 5-methoxy-2-methyl-indol-1-ylamine (550 mg, 3.1 mmol) in DMF (4 mL) is stirred at 50° C. for 15 min. The mixture is treated with DMTMM (856 mg, 3.1 mmol) and stirred at 50° C. for 1 h. The mixture is concentrated in vacuo, diluted with EtOAc (50 mL), and washed with saturated aqueous Na2CO3 (50 mL). The organic layer is separated, dried (Na2SO4), filtered and concentrated in vacuo. The residue is purified by silica gel chromatography eluting with 30% EtOAc in heptane to afford 2-(3-fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (5-methoxy-2-methyl-indol-1-yl)-amide (180 mg, 15%, 2 steps). MS: 391 (M+H); 1H NMR (300 MHz, DMSO-d6): δ 9.23 (s, 1H), 8.34 (d, 1H), 8.18 (d, 1H), 7.63 (m, 1H), 7.46 (m, 1H), 7.31 (d, 1H), 7.02 (d, 1H), 6.77 (m, 1H), 6.25 (s, 1H), 3.76 (s, 3H), 2.77 (s, 3H), 2.34 (s, 3H).

Workup

  1. concentrationThe mixture is concentrated in vacuo
  2. additiondiluted with EtOAc (50 mL)
  3. washwashed with saturated aqueous Na2CO3 (50 mL)
  4. customThe organic layer is separated
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue is purified by silica gel chromatography
  9. washeluting with 30% EtOAc in heptane

Sources & evidence

ORD record
ord-e7fc32298f1442da9c8d69ab771deb57
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

Loading…