4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride → HCID 59200032, compound

HRID 2382076Notes

Reaction equation

HRID 2382076 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.[F:18][C:19]1[CH:20]=[CH:21][CH:22]=[C:23]2[C:27]=1[N:26]([NH2:28])[CH:25]=[C:24]2[CH3:29].C[N+]1(C2N=C(OC)N=C(OC)N=2)CCOCC1.[Cl-]>CN(C=O)C>[F:18][C:19]1[CH:20]=[CH:21][CH:22]=[C:23]2[C:27]=1[N:26]([NH:28][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:25]=[C:24]2[CH3:29]

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 68555827HCID 68555827, compound

Product 1

HCID 59200032HCID 59200032, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 2-(3-fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (1.34 mmol) and 7-fluoro-3-methyl-indol-1-ylamine (342 mg, 1.47 mmol) in DMF (15 mL) is stirred at 50° C. for 1 h. The mixture is treated with DMTMM (407 mg, 1.47 mmol) and stirred at 50° C. for 4 h. The mixture is concentrated in vacuo, diluted with Et2O (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% DCM in EtOAc to afford 2-(3-fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (7-fluoro-3-methyl-indol-1-yl)-amide (241 mg, 48%). MS: 379 (M+H); 1H NMR (300 MHz, DMSO-d6): δ 9.05 (s, 1H), 8.32 (d, 1H), 8.18 (d, 1H), 7.64 (m, 1H), 7.45 (m, 1H), 7.40 (m, 1H), 7.31 (s, 1H), 7.05 (m, 2H), 2.74 (s, 3H), 2.29 (s, 3H).

Workup

  1. concentrationThe mixture is concentrated in vacuo
  2. additiondiluted with Et2O (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 0%-100% DCM in EtOAc

Sources & evidence

ORD record
ord-6af418da54de41b192effcab18fe223f
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

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