Methylamine hydrochloride → Ammonium Acetate

HRID 219355Notes

Reaction equation

[CH2:1]([N:3]([C:8]1[C:9]([C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([C:33](=[O:44])[NH:34][C:35]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)([CH3:37])[CH3:36])[CH:28]=2)=[CH:10][C:11]2[N:12]([N:14]=[C:15]([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)[C:16]=2[C:17]([OH:19])=[O:18])[CH:13]=1)[S:4]([CH3:7])(=[O:6])=[O:5])[CH3:2].Cl.[CH3:46][NH2:47]>>[C:17]([O-:19])(=[O:18])[CH3:16].[NH4+:3].[CH2:1]([N:3]([C:8]1[C:9]([C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([C:33](=[O:44])[NH:34][C:35]([C:38]3[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=3)([CH3:36])[CH3:37])[CH:28]=2)=[CH:10][C:11]2[N:12]([N:14]=[C:15]([C:20]3[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=3)[C:16]=2[C:17]([NH:47][CH3:46])=[O:18])[CH:13]=1)[S:4]([CH3:7])(=[O:6])=[O:5])[CH3:2]

Participants

Reactant 2

HCID 6364545Methylamine hydrochloride

HCID 674197986-(N-ethylmethylsulfonamido)-2-(4-fluorophenyl)-5-(3-(2-phenylpropan-2-ylcarbamoyl)phenyl)pyrazolo[1,5-a]pyridine-3-carboxylic acid

Product 2

HCID 517165Ammonium Acetate

HCID 46842507HCID 46842507, compound

Procedure

6-(N-ethylmethylsulfonamido)-2-(4-fluorophenyl)-N-methyl-5-(3-(2-phenylpropan-2-ylcarbamoyl)phenyl)pyrazolo[1,5-a]pyridine-3-carboxamide was prepared from 6-(N-ethylmethylsulfonamido)-2-(4-fluorophenyl)-5-(3-(2-phenylpropan-2-ylcarbamoyl)phenyl)pyrazolo[1,5-a]pyridine-3-carboxylic acid (0.030 g, 0.049 mmol) and methylamine hydrochloride (0.014 g, 0.19 mmol). The resultant residue was purified using preparative HPLC (Waters-Xbridge, 50×100 mm, 5 micron, C18 column; 0.1M ammonium acetate, 0-100% B (B=5% H2O/CH3CN)/A (A=95% H2O/CH3CN), 10 min. gradient) to afford 6-(N-ethylmethylsulfonamido)-2-(4-fluorophenyl)-N-methyl-5-(3-(2-phenylpropan-2-ylcarbamoyl)phenyl)pyrazolo[1,5-a]pyridine-3-carboxamide as a white solid. Preparative HPLC: retention time: 8.5 min. 1H NMR (500 MHz, DMSO-d6) δ ppm 9.25 (s, 1H), 8.36 (s, 1H), 8.05 (q, J=4.37 Hz, 1H), 8.02 (s, 1H), 7.89-7.95 (m, 3H), 7.78 (s, 1H), 7.75 (d, J=7.63 Hz, 1H), 7.58 (t, J=7.78 Hz, 1H), 7.40 (d, J=7.32 Hz, 2H), 7.35 (t, J=8.85 Hz, 2H), 7.29 (t, J=7.78 Hz, 2H), 7.18 (t, J=7.32 Hz, 1H), 3.52 (s, 1H), 3.21 (s, 3H), 3.12 (s, 1H), 2.77 (d, J=4.58 Hz, 3H), 1.69 (s, 6H), 0.95 (t, J=7.17 Hz, 3H). LCMS retention time: 2.213 min. LC data was recorded on a Shimadzu LC-10AS liquid chromatograph equipped with a Sunfire C18, 5 micron, C18, 4.6×50 mm column using a SPD-10AV UV-Vis detector at a detector wave length of 220 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 628 (MH+).

Workup

customThe resultant residue was purified

Sources & evidence

ORD record: ord-e3893cf7aaf4494099f221160e1772d0
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08198449B2

Reaction notes

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