Dimethylformamide → HCID 10004104, compound

HRID 2376815Notes

Reaction equation

HRID 2376815 reaction equation
C1(O[C:8](=[O:30])[NH:9][C:10]2[CH:15]=[C:14]([O:16][C:17]3[CH:18]=[C:19]4[C:23](=[CH:24][CH:25]=3)[N:22]([C:26](=[O:29])[NH:27][CH3:28])[CH:21]=[CH:20]4)[N:13]=[CH:12][N:11]=2)C=CC=CC=1.[CH2:31]([N:33]([CH2:38][CH3:39])[CH2:34][CH2:35][CH2:36][NH2:37])[CH3:32].C[N:41](C)C=O>>[CH3:28][NH:27][C:26]([N:22]1[C:23]2[C:19](=[CH:18][C:17]([O:16][C:14]3[CH:15]=[C:10]([NH:9][C:8]([NH:41][NH:37][CH2:36][CH2:35][CH2:34][N:33]([CH2:38][CH3:39])[CH2:31][CH3:32])=[O:30])[N:11]=[CH:12][N:13]=3)=[CH:25][CH:24]=2)[CH:20]=[CH:21]1)=[O:29]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 61011N,N-Diethyl-1,3-propanediamineHCID 21949234HCID 21949234, compound

Product 1

HCID 10004104HCID 10004104, compoundYield 70%

Procedure

Phenyl(6-(1-methylcarbamoyl-1H-indol-5-yloxy)pyrimidin-4-yl)carbamate (161 mg, 0.400 mmol) was dissolved in N,N-dimethylformamide (1.0 ml), and 3-(diethylamino)propylamine (130 mg, 1.00 mmol) was added while the reaction mixture was stirred at room temperature. After the reaction mixture was stirred overnight, the reaction mixture was partitioned between ethyl acetate and water. The organic layer was washed with water and brine, and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was purified by NH silica gel column chromatography (eluent; ethyl acetate:methanol=50:1). The crystals were precipitated from ethyl acetate-hexane, filtered off, and dried under aeration to yield the title compound (123 mg, 0.280 mmol, 70%) as white crystals.

Workup

  1. stirringAfter the reaction mixture was stirred overnight
  2. customthe reaction mixture was partitioned between ethyl acetate and water
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off
  6. customthe residue was purified by NH silica gel column chromatography (eluent; ethyl acetate:methanol=50:1)
  7. customThe crystals were precipitated from ethyl acetate-hexane
  8. filtrationfiltered off
  9. customdried under aeration

Sources & evidence

ORD record
ord-36e62eccb09b442db4bfa2789ad2674d
Source dataset
uspto-grants-2008_12
Patent number
US07468380B2

Reaction notes

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