Water → HCID 66812907, compound

HRID 389302Notes

Reaction equation

HRID 389302 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH3:25])=[CH:5][C:6]([CH2:12][C:13]2[C:14]([CH3:24])=[N:15][N:16]([CH2:19][CH2:20][C:21]([OH:23])=O)[C:17]=2[CH3:18])=[C:7]2[C:11]=1[CH2:10][CH2:9][CH2:8]2.C(C1NC=CN=1)(C1NC=CN=1)=O.[CH:38]([NH2:41])([CH3:40])[CH3:39].O>O1CCCC1.CCCCCC>[CH:38]([NH:41][C:21](=[O:23])[CH2:20][CH2:19][N:16]1[C:17]([CH3:18])=[C:13]([CH2:12][C:6]2[CH:5]=[C:4]([CH3:25])[C:3]([O:2][CH3:1])=[C:11]3[C:7]=2[CH2:8][CH2:9][CH2:10]3)[C:14]([CH3:24])=[N:15]1)([CH3:40])[CH3:39]

Participants

7

Reactant 4

HCID 962WaterHCID 6363IsopropylamineHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 25125866HCID 25125866, compound

Product 1

HCID 66812907HCID 66812907, compoundYield 72.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
72.5 °C

Procedure

To the solution of 3-[4-(7-Methoxy-6-methyl-indan-4-ylmethyl)-3,5-dimethyl-pyrazol-1-yl]-propionic acid (1.0 gm, 0.00292 mole) in Tetrahydrofuran (20 ml), Carbonyl-diimidazole (0.62 gm, 0.0038 mole) was added at 20-30° C. The reaction mixture was heated and stirred for an hour at 70-75° C. A solution of Isopropyl amine (0.3 ml, 0.00367 mole) in Tetrahydrofuran (5 ml) was added at 20-30° C. The reaction mixture was further stirred at 70° C. for 4 hours. The reaction mixture was cooled and poured into water (50 ml) and extracted with Ethyl acetate (2×100 ml). The Ethyl acetate layer was dried over Sodium sulphate, distilled under vacuum to get a crude product which was stirred in Hexane (20 ml) and filtered to give 810 mg of desired product as a solid.

Workup

  1. temperatureThe reaction mixture was heated
  2. stirringThe reaction mixture was further stirred at 70° C. for 4 hours
  3. temperatureThe reaction mixture was cooled
  4. extractionextracted with Ethyl acetate (2×100 ml)
  5. dry with materialThe Ethyl acetate layer was dried over Sodium sulphate
  6. distillationdistilled under vacuum
  7. customto get a crude product which
  8. filtrationfiltered

Sources & evidence

ORD record
ord-bd02d527ab68438fba56e7459240d521
Source dataset
uspto-grants-2013_02
Patent number
US08378118B2

Reaction notes

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