1-(2-Pyridyl)cyclopropylamine Dihydrochloride → Methyl 2-(4-fluorophenyl)-6-(N-(2-hydroxyethyl)methylsulfonamido)-5-(3-(1-(pyridin-2-yl)cyclopropylcarbamoyl)phenyl)pyrazolo[1,5-a]pyridine-3-carboxylate

HRID 44008Notes

Reaction equation

HRID 44008 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:33]([C:34]([O:36][CH3:37])=[O:35])=[C:11]3[CH:12]=[C:13]([C:24]4[CH:25]=[C:26]([CH:30]=[CH:31][CH:32]=4)[C:27]([OH:29])=O)[C:14]([N:16]([CH2:21][CH2:22][OH:23])[S:17]([CH3:20])(=[O:19])=[O:18])=[CH:15][N:10]3[N:9]=2)=[CH:4][CH:3]=1.Cl.Cl.[N:40]1[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=1[C:46]1([NH2:49])[CH2:48][CH2:47]1>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:33]([C:34]([O:36][CH3:37])=[O:35])=[C:11]3[CH:12]=[C:13]([C:24]4[CH:32]=[CH:31][CH:30]=[C:26]([C:27](=[O:29])[NH:49][C:46]5([C:41]6[CH:42]=[CH:43][CH:44]=[CH:45][N:40]=6)[CH2:48][CH2:47]5)[CH:25]=4)[C:14]([N:16]([CH2:21][CH2:22][OH:23])[S:17]([CH3:20])(=[O:19])=[O:18])=[CH:15][N:10]3[N:9]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 533931811-(2-Pyridyl)cyclopropylamine DihydrochlorideHCID 592337323-(2-(4-fluorophenyl)-6-(N-(2-hydroxyethyl)methylsulfonamido)-3-(methoxycarbonyl)pyrazolo[1,5-a]pyridin-5-yl)benzoic acid

Product 1

HCID 59233739Methyl 2-(4-fluorophenyl)-6-(N-(2-hydroxyethyl)methylsulfonamido)-5-(3-(1-(pyridin-2-yl)cyclopropylcarbamoyl)phenyl)pyrazolo[1,5-a]pyridine-3-carboxylate

Procedure

Methyl 2-(4-fluorophenyl)-6-(N-(2-hydroxyethyl)methylsulfonamido)-5-(3-(1-(pyridin-2-yl)cyclopropylcarbamoyl)phenyl)pyrazolo[1,5-a]pyridine-3-carboxylate was prepared from 3-(2-(4-fluorophenyl)-6-(N-(2-hydroxyethyl)methylsulfonamido)-3-(methoxycarbonyl)pyrazolo[1,5-a]pyridin-5-yl)benzoic acid (0.05 g, 0.10 mmol) and 1-(pyridin-2-yl)cyclopropanamine dihydrochloride (0.03 g, 0.15 mmol). LCMS: retention time: 1.473 min. LC data was recorded on a Shimadzu LC-10AS liquid chromatograph equipped with a Waters-Sunfire, 5 micron, C18, 4.6×50 mm column using a SPD-10AV UV-Vis detector at a detector wave length of 254 nM. The elution conditions employed a flow rate of 4 mL/min, a gradient of 100% solvent A/0% solvent B to 0% solvent A/100% solvent B, a gradient time of 3 min, a hold time of 1 min, and an analysis time of 4 min where solvent A was 10% CH3CN/90% H2O/10 mM TFA and solvent B was 10% H2O/90% CH3CN/10 mM TFA. MS data was determined using a Micromass Platform for LC in electrospray mode. m/z 644 (MH+).

Workup

  1. customequipped with a Waters-Sunfire, 5 micron, C18, 4.6×50 mm column
  2. washThe elution conditions
  3. customa gradient time of 3 min
  4. customa hold time of 1 min
  5. customan analysis time of 4 min where solvent A was 10% CH3CN/90% H2O/10 mM TFA and solvent B

Sources & evidence

ORD record
ord-38d08ffff4ec45c7ad50f4867601ff6b
Source dataset
uspto-grants-2013_09
Patent number
US08536338B2

Reaction notes

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