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4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride → HCID 68554534, compound

HRID 2382037
Notes
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Reaction equation

HRID 2382037 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].[CH3:19][C:20]1[C:25]([C:26](O)=[O:27])=[CH:24][N:23]=[C:22]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=2)[N:21]=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:26]([C:25]2[C:20]([CH3:19])=[N:21][C:22]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=3)=[N:23][CH:24]=2)=[O:27])[CH:8]=1)([CH3:6])[CH3:5]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 27340594-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chlorideHCID 617020254-Methyl-2-(pyridin-2-yl)pyrimidine-5-carboxylic acidHCID 68554564HCID 68554564, compound

Product 1

HCID 68554534HCID 68554534, 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 4-methyl-2-pyridin-2-yl-pyrimidine-5-carboxylic acid (201 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 dried (Na2SO4), filtered and concentrated in vacuo to afford 2-{5-fluoro-1-[(4-methyl-2-pyridin-2-yl-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. dry with materialThe combined organic layer is dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c18643226afa49f9b7cc2aefa4092015
Source dataset
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08258130B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes