4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride → HCID 59199965, compound

HRID 2382079Notes

Reaction equation

HRID 2382079 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][S:19]([C:22]1[CH:23]=[C:24]2[C:28](=[CH:29][CH:30]=1)[N:27]([NH2:31])[CH:26]=[C:25]2[CH3:32])(=[O:21])=[O:20].C[N+]1(C2N=C(OC)N=C(OC)N=2)CCOCC1.[Cl-]>CN(C=O)C.CCOC(C)=O>[CH3:18][S:19]([C:22]1[CH:23]=[C:24]2[C:28](=[CH:29][CH:30]=1)[N:27]([NH:31][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])[CH:26]=[C:25]2[CH3:32])(=[O:21])=[O:20]

Participants

6

Reactant 3

HCID 27340594-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chlorideHCID 617025872-(3-Fluorophenyl)-4-methylpyrimidine-5-carboxylic acidHCID 68555546HCID 68555546, compound

Product 1

HCID 59199965HCID 59199965, compoundYield 14%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 2-(3-fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (1.77 mmol) and 5-methanesulfonyl-3-methyl-indol-1-ylamine (452 mg, 1.95 mmol) in DMF (15 mL) is stirred at rt for 1 h. The mixture is treated with DMTMM (538 mg, 1.95 mmol) and stirred at 60° C. for 1.5 h. The mixture is 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 0%-100% EtOAc in heptane, and then by triturating in Et2O to afford 2-(3-fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (5-methanesulfonyl-3-methyl-indol-1-yl)-amide (106 mg, 14%). MS: 439 (M+H); 1H NMR (300 MHz, DMSO-d6): δ 9.15 (s, 1H), 8.37 (d, 1H), 8.24 (m, 2H), 7.82 (m, 1H), 7.59 (d, 1H), 7.54 (m, 1H), 7.34 (s, 1H), 7.29 (m, 1H), 3.13 (s, 3H), 2.83 (s, 3H), 2.42 (s, 3H).

Workup

  1. washwashed with saturated aqueous Na2CO3 (50 mL)
  2. customThe organic layer is separated
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified by silica gel chromatography
  7. washeluting with 0%-100% EtOAc in heptane
  8. customby triturating in Et2O

Sources & evidence

ORD record
ord-95afcd1de5ec4601ac5b257a613ebf56
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

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