Pyridine → HCID 59548739, compound

HRID 1810973Notes

Reaction equation

HRID 1810973 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([CH3:7])[N:4]([CH2:8][C:9]([OH:11])=O)[N:3]=1.[N:12]1C=CC=CC=1.[Cl:18][C:19]1[CH:20]=[C:21]([CH:39]=[CH:40][CH:41]=1)[C:22]([NH:24][C:25]1[CH:30]=[C:29]([Cl:31])[CH:28]=C[C:26]=1[N:32]1[CH2:38][CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1)=[O:23]>CN(C)C=O>[Cl:18][C:19]1[CH:20]=[C:21]([CH:39]=[CH:40][CH:41]=1)[C:22]([NH:24][C:25]1[C:26]([N:32]2[CH2:38][CH2:37][CH2:36][N:35]([C:9](=[O:11])[CH2:8][N:4]3[C:5]([CH3:7])=[CH:6][C:2]([CH3:1])=[N:3]3)[CH2:34][CH2:33]2)=[N:12][CH:28]=[C:29]([Cl:31])[CH:30]=1)=[O:23]

Participants

5

Reactant 3

HCID 1049PyridineHCID 572875(3,5-Dimethyl-1H-pyrazol-1-yl)acetic acidHCID 66609817HCID 66609817, compound

Product 1

HCID 59548739HCID 59548739, compoundYield 29.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To solution of (3,5-dimethyl-pyrazol-1-yl)-acetic acid (0.010 g, 0.068 mmol) in N,N-dimethylformamide (2 mL) is added 0.006 mL (0.071 mmol) of pyridine followed by) tetramethyluroniumhydroxybenzotriazolehexaflourophosphate (0.123 g, 0.324 mmol). The mixture stirred for 1 hour. To this is added 3-chloro-N-(5-chloro-2-[1,4]diazepan-1-yl-phenyl)-benzamide (0.025 g, 0.068 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 3-chloro-N-(5-chloro-2-{4-[2-(3,5-dimethyl-pyrazol-1-yl)-acetyl]-[1,4]diazepan-1-yl}-pyridin-3-yl)-benzamide in 29% yield. MS MH+=501.8

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-a75d4433e7dd486b809a91c4751e7489
Source dataset
uspto-grants-2013_01
Patent number
US08362249B2

Reaction notes

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