Triethylamine → HCID 69028041, compound

HRID 219723Notes

Reaction equation

HRID 219723 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=1.C(N(CC)CC)C.OC1C2N=NNC=2C=CC=1.[C:28]([C:32]1[N:37]=[C:36]([N:38]2[CH2:43][CH2:42][N:41]([CH2:44][CH2:45][CH2:46][CH2:47][NH2:48])[CH2:40][CH2:39]2)[CH:35]=[C:34]([CH:49]2[CH2:52][CH2:51][CH2:50]2)[N:33]=1)([CH3:31])([CH3:30])[CH3:29].[ClH:53].C(N=C=NCCCN(C)C)C>CN(C)C=O>[ClH:53].[C:28]([C:32]1[N:37]=[C:36]([N:38]2[CH2:39][CH2:40][N:41]([CH2:44][CH2:45][CH2:46][CH2:47][NH:48][C:6](=[O:8])[C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:10][CH:9]=3)[CH2:42][CH2:43]2)[CH:35]=[C:34]([CH:49]2[CH2:52][CH2:51][CH2:50]2)[N:33]=1)([CH3:31])([CH3:29])[CH3:30]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 99734-Fluorobenzoic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 690260674-[4-(2-tert-Butyl-6-cyclobutyl-pyrimidin-4-yl)piperazin-1-yl]-butylamineHCID 178418300HCID 178418300, compound

Product 1

HCID 69028041HCID 69028041, compoundYield 74.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.45 g of 4-fluorobenzoic acid (3.21 mmol) and 0.98 g of triethylamine (9.7 mmol) were dissolved in 30 ml of dimethylformamide. At room temperature, 0.5 g of hydroxybenzotriazole (HOBt, 3.7 mmol), 1.2 g of 4-[4-(2-tert-butyl-6-cyclobutyl-pyrimidin-4-yl)-piperazin-1-yl]-butylamine (3.47 mmol), and 0.7 g of N-ethyl-N′-(3-dimethylaminopropyl)-carbodiimide hydrochloride (EDCl, 3.65 mmol) were added and the mixture was stirred for 68 h. The reaction mixture was partitioned between water and ethyl acetate. The organic phase was dried over magnesium sulfate, filtered, and concentrated to dryness. The crude product was purified by chromatography on silica gel using dichloromethane-methanol (2%). The oily residue was re-dissolved in isopropanol and 1 N hydrochloric acid in diisopropyl ether was added. The resulting precipitate was filtered and dried to yield 1.2 g of the title compound.

Workup

  1. customThe reaction mixture was partitioned between water and ethyl acetate
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated to dryness
  5. customThe crude product was purified by chromatography on silica gel
  6. dissolutionThe oily residue was re-dissolved in isopropanol
  7. addition1 N hydrochloric acid in diisopropyl ether was added
  8. filtrationThe resulting precipitate was filtered
  9. customdried

Sources & evidence

ORD record
ord-6c3d1a860e7346bcad1ca868a2caf423
Source dataset
uspto-grants-2012_06
Patent number
US08202868B2

Reaction notes

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