Ammonium Chloride → HCID 66968349, compound

HRID 241350Notes

Reaction equation

HRID 241350 reaction equation
[Cl:1][C:2]1[CH:34]=[CH:33][C:5]([C:6]([N:8]2[CH2:13][CH2:12][N:11]([CH:14]3[CH:18]([OH:19])[CH2:17][N:16]([C:20]4[N:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[C:23]([C:30]([OH:32])=O)=[CH:22][N:21]=4)[CH2:15]3)[CH2:10][CH2:9]2)=[O:7])=[CH:4][CH:3]=1.C[N:36](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1.[NH4+].[Cl-]>CN(C=O)C.CCOC(C)=O>[Cl:1][C:2]1[CH:34]=[CH:33][C:5]([C:6]([N:8]2[CH2:9][CH2:10][N:11]([CH:14]3[CH:18]([OH:19])[CH2:17][N:16]([C:20]4[N:25]=[C:24]([C:26]([F:27])([F:28])[F:29])[C:23]([C:30]([NH2:36])=[O:32])=[CH:22][N:21]=4)[CH2:15]3)[CH2:12][CH2:13]2)=[O:7])=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66968377HCID 66968377, compound

Product 1

HCID 66968349HCID 66968349, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-{3-[4-(4-Chloro-benzoyl)-piperazin-1-yl]-4-hydroxy-pyrrolidin-1-yl}-4-trifluoromethyl-pyrimidine-5-carboxylic acid (1 eq) in DMF (1 mL), was added HATU (1.5 eq), DIPEA (4 eq) and HOBt (1.5 eq). The mixture was stirred at RT for 5 min. Then NH4Cl (2 eq) was added. The final reaction mixture was stirred at RT for overnight. EtOAc (2 mL) was added. The organic layer was washed with H2O (2×1 mL), dried over Na2SO4, and concentrated. The residue was purified by column chromatography (Ethyl acetate) to give the desired product as a white solid (35% yield). MS: (ESI), M/Z, 499 (M+1). Retention time: 1.56 min (FA-polar).

Workup

  1. customThe final reaction mixture
  2. stirringwas stirred at RT for overnight
  3. washThe organic layer was washed with H2O (2×1 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography (Ethyl acetate)

Sources & evidence

ORD record
ord-45f43251e3474d5c8bf1b8a65c571e82
Source dataset
uspto-grants-2014_02
Patent number
US08648197B2

Reaction notes

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