Diisopropylethylamine → HCID 66661811, compound

HRID 504313Notes

Reaction equation

HRID 504313 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:16]([OH:18])=O)[CH2:11][CH:10]([O:12][CH2:13][O:14][CH3:15])[CH2:9]2)=[CH:4][CH:3]=1.CC[N:21]([CH:25]([CH3:27])C)[CH:22]([CH3:24])C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.Cl.[NH:56]1[CH:60]=[CH:59][CH:58]([C:61]2C=CC=CN=2)[CH2:57]1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([C:16]([N:56]3[CH2:60][CH2:59][CH:58]([C:61]4[CH:24]=[CH:22][N:21]=[CH:25][CH:27]=4)[CH2:57]3)=[O:18])[CH2:9][CH:10]([O:12][CH2:13][O:14][CH3:15])[CH2:11]2)=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 516892Sodium BicarbonateHCID 22722155HCID 22722155, compoundHCID 66662174HCID 66662174, compound

Product 1

HCID 66661811HCID 66661811, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(4-chlorophenyl)-3-(methoxymethoxy)cyclobutanecarboxylic acid in methylene chloride was add DIEA, and the mixture was stirred for 10 minutes. Then BOP was added and the mixture was stirred for 20 minutes. Then 4-pyrrolin-3-ylpyridine hydrochloride was added and the resulting mixture was stirred at room temperature overnight. The completion of the reaction was determined by LCMS. The reaction mixture then was poured in to a saturated NaHCO3 aqueous solution and the resulting mixture was extract with CH2Cl2 (2×). The combined organic layers were dried over MgSO4, then filtered and then concentrated in-vacuo. The crude product was purified by flash column chromatography with MeOH/CH2Cl2 (1%, 3%, 5%, 7%) to afford the desired product (24.1 mg). The identification of the product was confirmed by LCMS and 1H NMR. LC/MS: 401.2 (M+H+).

Workup

  1. stirringthe mixture was stirred for 20 minutes
  2. stirringthe resulting mixture was stirred at room temperature overnight
  3. extractionthe resulting mixture was extract with CH2Cl2 (2×)
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in-vacuo
  7. customThe crude product was purified by flash column chromatography with MeOH/CH2Cl2 (1%, 3%, 5%, 7%)

Sources & evidence

ORD record
ord-ffd70bdcde574a749abcfadd0fa84b67
Source dataset
uspto-grants-2010_08
Patent number
US07776874B2

Reaction notes

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