Diisopropylethylamine → HCID 66661811, compound

HRID 2275569Notes

Reaction equation

HRID 2275569 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-d91ef80cfd374aab9bb0ad20650baa62
Source dataset
uspto-grants-2015_09
Patent number
US09126927B2

Reaction notes

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