4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride → HCID 68554244, compound

HRID 2382039Notes

Reaction equation

HRID 2382039 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C:4]([C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([F:16])[CH:14]=2)[N:9]([NH2:17])[CH:8]=1)([CH3:6])[CH3:5].[F:19][C:20]1[CH:21]=[C:22]([C:26]2[N:31]=[C:30]([CH3:32])[C:29]([C:33](O)=[O:34])=[CH:28][N:27]=2)[CH:23]=[CH:24][CH:25]=1.C[N+]1(C2N=C(OC)N=C(OC)N=2)CCOCC1.[Cl-]>CN(C=O)C>[CH3:1][O:2][C:3](=[O:18])[C:4]([C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([F:16])[CH:14]=2)[N:9]([NH:17][C:33]([C:29]2[C:30]([CH3:32])=[N:31][C:26]([C:22]3[CH:23]=[CH:24][CH:25]=[C:20]([F:19])[CH:21]=3)=[N:27][CH:28]=2)=[O:34])[CH:8]=1)([CH3:6])[CH3:5]

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 68554564HCID 68554564, compound

Product 1

HCID 68554244HCID 68554244, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 2-(1-amino-5-fluoro-1H-indol-3-yl)-2-methyl-propionic acid methyl ester (0.85 mmol) and 2-(3-fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (217 mg, 0.935 mmol) in DMF (8.5 mL) is stirred at 40° C. for 0.5 h. The mixture is treated with DMTMM (246 mg, 0.89 mmol) and stirred at 60° C. for 1 h. The mixture is concentrated in vacuo, diluted with saturated aqueous Na2CO3 (20 mL), and extracted with EtOAc (3×20 mL). The combined organic layer is separated, dried (Na2SO4), filtered and concentrated in vacuo to afford 2-(5-fluoro-1-{[2-(3-fluoro-phenyl)-4-methyl-pyrimidine-5-carbonyl]-amino}-1H-indol-3-yl)-2-methyl-propionic acid methyl ester, which is used in the next step without further purification.

Workup

  1. concentrationThe mixture is concentrated in vacuo
  2. additiondiluted with saturated aqueous Na2CO3 (20 mL)
  3. extractionextracted with EtOAc (3×20 mL)
  4. customThe combined organic layer is separated
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bfbf5103a72b451cb21a5569177ea127
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

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