Pyridine → HCID 66599594, compound

HRID 1810968Notes

Reaction equation

HRID 1810968 reaction equation
[Cl:1][C:2]1[C:3]([CH3:12])=N[N:5]([CH2:8][C:9](O)=O)[C:6]=1[CH3:7].N1C=CC=CC=1.[Cl:19][C:20]1[CH:21]=[C:22]([NH:32][C:33](=[O:44])[C:34]2[CH:39]=[CH:38][CH:37]=[C:36]([C:40]([F:43])([F:42])[F:41])[CH:35]=2)[C:23]([N:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)=[N:24][CH:25]=1.CN(C)[CH:47]=[O:48]>>[Cl:19][C:20]1[CH:21]=[C:22]([NH:32][C:33](=[O:44])[C:34]2[CH:39]=[CH:38][CH:37]=[C:36]([C:40]([F:42])([F:43])[F:41])[CH:35]=2)[C:23]([N:26]2[CH2:31][CH2:30][N:29]([C:47](=[O:48])[CH2:9][CH:8]3[C:3]([CH3:12])=[C:2]([Cl:1])[C:6]([CH3:7])=[N:5]3)[CH2:28][CH2:27]2)=[N:24][CH:25]=1

Participants

5

Reactant 4

HCID 1049PyridineHCID 6228DimethylformamideHCID 919266(4-Chloro-3,5-dimethyl-1H-pyrazol-1-yl)acetic acidHCID 57516323HCID 57516323, compound

Product 1

HCID 66599594HCID 66599594, compoundYield 21%

Procedure

To solution of (4-chloro-3,5-dimethyl-pyrazol-1-yl)-acetic acid (0.051 g, 0.160 mmol) in N,N-dimethylformamide (2 mL) is added pyridine (0.006 mL, 0.07 mmol) followed by 0.123 g (0.324 mmol) of tetramethyluroniumhydroxybenzotriazolehexaflourophosphate. The mixture stirred for 1 h. To this is added of N-(5-chloro-2-piperazin-1-yl-pyridin-3-yl)-3-trifluoromethyl-benzamide (0.031 g, 0.162 mmol). The mixture is allowed to stir overnight. The mixture is concentrated under reduced pressure and is purified by reverse phase HPLC to provide 0.010 g of N-(5-chloro-2-{4-[2-(4-chloro-3,5-dimethyl-2H-pyrrol-2-yl)-acetyl]-piperazin-1-yl}-pyridin-3-yl)-3-trifluoromethyl-benzamide in 21% yield. MS; MH+=558.8

Workup

  1. stirringto stir overnight
  2. concentrationThe mixture is concentrated under reduced pressure
  3. customis purified by reverse phase HPLC

Sources & evidence

ORD record
ord-c77a8cb7dd244e189ed39272ace73b95
Source dataset
uspto-grants-2013_01
Patent number
US08362249B2

Reaction notes

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