1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 52919611, compound

HRID 1615378Notes

Reaction equation

HRID 1615378 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:16]=[C:15]3[C:11]([CH:12]=[CH:13][N:14]3[C:17]3[N:22]=[CH:21][N:20]=[C:19]([NH2:23])[CH:18]=3)=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[Cl:24][C:25]1[CH:33]=[CH:32][C:28]([C:29](O)=[O:30])=[CH:27][C:26]=1[C:34]([F:37])([F:36])[F:35].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.C(=O)(O)[O-].[Na+]>C1COCC1.C(OCC)(=O)C.O>[NH2:23][C:19]1[N:20]=[CH:21][N:22]=[C:17]([N:14]2[C:15]3[C:11](=[CH:10][CH:9]=[C:8]([C:4]4[CH:3]=[C:2]([NH:1][C:29](=[O:30])[C:28]5[CH:32]=[CH:33][C:25]([Cl:24])=[C:26]([C:34]([F:37])([F:35])[F:36])[CH:27]=5)[CH:7]=[CH:6][CH:5]=4)[CH:16]=3)[CH:12]=[CH:13]2)[CH:18]=1

Participants

9

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27738574-Chloro-3-(trifluoromethyl)benzoic acidHCID 67203782HCID 67203782, compound

Product 1

HCID 52919611HCID 52919611, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

6-(6-(3-Aminophenyl)-1H-indol-1-yl)pyrimidin-4-amine (15 mg, 0.050 mmol), 4-chloro-3-(trifluoromethyl)benzoic acid (16.8 mg, 0.075 mmol) and HOBt (6.8 mg, 0.050 mmol) were dissolved in THF (1 mL). At room temperature, EDCI (28.8 mg, 0.15 mmol) was added. The reaction solution was stirred at room temperature for 15 hours and the reaction mixture was added to saturated sodium bicarbonate aqueous solution. After adding water and ethyl acetate, the aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with brine, dried with anhydrous magnesium sulfate, and concentrated under reduced pressure. Purification of the residue by column chromatography (silica gel, EA:Hx=1:4→MC:MeOH=20:1) yielded the target compound.

Workup

  1. extractionthe aqueous layer was extracted with ethyl acetate
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried with anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customPurification of the residue by column chromatography (silica gel, EA:Hx=1:4→MC:MeOH=20:1)
  6. customyielded the target compound

Sources & evidence

ORD record
ord-8900a4ee73b24523b2070ac055f651ad
Source dataset
uspto-grants-2014_07
Patent number
US08765749B2

Reaction notes

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