1,2-Dichloroethane → HCID 11526678, compound

HRID 2266686Notes

Reaction equation

HRID 2266686 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:9]=[N:10][N:11]([C:13]([CH3:18])([CH3:17])[C:14](O)=[O:15])[CH:12]=2)=[CH:4][C:3]=1[O:19][CH:20]([C:22]1[C:27]([Cl:28])=[CH:26][CH:25]=[C:24]([F:29])[C:23]=1[Cl:30])[CH3:21].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.[CH3:45][N:46]([CH3:51])[CH2:47][CH2:48][CH2:49][NH2:50]>CN(C=O)C>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:9]=[N:10][N:11]([C:13]([CH3:18])([CH3:17])[C:14]([NH:50][CH2:49][CH2:48][CH2:47][N:46]([CH3:51])[CH3:45])=[O:15])[CH:12]=2)=[CH:4][C:3]=1[O:19][CH:20]([C:22]1[C:27]([Cl:28])=[CH:26][CH:25]=[C:24]([F:29])[C:23]=1[Cl:30])[CH3:21]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 7993N,N-Dimethyl-1,3-propanediamineHCID 757711-HydroxybenzotriazoleHCID 11662438HCID 11662438, compound

Product 1

HCID 11526678HCID 11526678, compoundYield 14.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(4-{6-amino-5-[1-(2,6-dichloro-3-fluoro-phenyl)-ethoxy]-pyridin-3-yl}-pyrazol-1-yl)-2-methyl-propionic acid (1.00 g, 2.20 mmol) in DMF (5.5 mL) were added HOBT (300 mg, 2.20 mmol), EDC (633 mg, 3.30 mmol), and N,N-dimethyl-propane-1,3-diamine (225 mg, 2.20 mmol). The reaction was stirred overnight at room temperature. The reaction was then purified by reversed phase C-18 prep HPLC eluting with acetonitrile/water with 0.1% acetic acid to afford 2-(4-{6-amino-5-[1-(2,6-dichloro-3-fluoro-phenyl)-ethoxy]-pyridin-3-yl}-pyrazol-1-yl)-N-(3-dimethylamino-propyl)-isobutyramide (170 mg, 14% yield).

Workup

  1. customThe reaction was then purified by reversed phase C-18 prep HPLC
  2. washeluting with acetonitrile/water with 0.1% acetic acid

Sources & evidence

ORD record
ord-d4f6eeeab7b640fc9dda075744a634f5
Source dataset
uspto-grants-2010_12
Patent number
US07858643B2

Reaction notes

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