Methylamine hydrochloride → Ammonium Acetate

HRID 219356Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:39]([C:40]([OH:42])=[O:41])=[C:11]3[CH:12]=[C:13]([C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([C:27](=[O:38])[NH:28][C:29]([C:32]5[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=5)([CH3:31])[CH3:30])[CH:22]=4)[C:14]([NH:16][S:17]([CH3:20])(=[O:19])=[O:18])=[CH:15][N:10]3[N:9]=2)=[CH:4][CH:3]=1.Cl.[CH3:44][NH2:45]>>[C:40]([O-:42])(=[O:41])[CH3:39].[NH4+:9].[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:39]([C:40]([NH:45][CH3:44])=[O:41])=[C:11]3[CH:12]=[C:13]([C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([C:27](=[O:38])[NH:28][C:29]([C:32]5[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=5)([CH3:31])[CH3:30])[CH:22]=4)[C:14]([NH:16][S:17]([CH3:20])(=[O:18])=[O:19])=[CH:15][N:10]3[N:9]=2)=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 6364545Methylamine hydrochloride

HCID 674188772-(4-Fluorophenyl)-6-(methylsulfonamido)-5-(3-(2-phenylpropan-2-ylcarbamoyl)phenyl)pyrazolo[1,5-a]pyridine-3-carboxylic acid

Product 2

HCID 517165Ammonium Acetate

HCID 592337312-(4-fluorophenyl)-N-methyl-6-(methylsulfonamido)-5-(3-(2-phenylpropan-2-ylcarbamoyl)phenyl)pyrazolo[1,5-a]pyridine-3-carboxamide

Procedure

2-(4-fluorophenyl)-N-methyl-6-(methylsulfonamido)-5-(3-(2-phenylpropan-2-ylcarbamoyl)phenyl)pyrazolo[1,5-a]pyridine-3-carboxamide was prepared from 2-(4-fluorophenyl)-6-(methylsulfonamido)-5-(3-(2-phenylpropan-2-ylcarbamoyl)phenyl)pyrazolo[1,5-a]pyridine-3-carboxylic acid (0.088 g, 0.090 mmol) and methylamine hydrochloride (0.024 g, 0.36 mmol). The resultant residue was purified using preparative HPLC (Waters-Xbridge, 50×100 mm, 5 micron, C18 column; 0.1M ammonium acetate, 10-80% B (B=5% H2O/CH3CN)/A (A=95% H2O/CH3CN), 20 min. gradient) to afford 2-(4-fluorophenyl)-N-methyl-6-(methylsulfonamido)-5-(3-(2-phenylpropan-2-ylcarbamoyl)phenyl)pyrazolo[1,5-a]pyridine-3-carboxamide as a white solid. Preparative HPLC retention time: 14 min. 1H NMR (500 MHz, DMSO-d6) δ ppm 9.43 (br. s., 1H), 8.82-8.92 (m, 3H), 8.46 (s, 3H), 8.04 (s, 4H), 7.88-7.98 (m, 13H), 7.69-7.78 (m, 7H), 7.54-7.62 (m, 4H), 7.41 (d, J=7.93 Hz, 7H), 7.26-7.36 (m, 14H), 7.18 (t, J=7.17 Hz, 3H), 2.84 (s, 10H), 2.71-2.80 (m, 11H), 1.65-1.75 (m, 21H). LCMS retention time: 2.002 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 600 (MH+).

Workup

customThe resultant residue was purified

Sources & evidence

ORD record: ord-bfad8824f5f240c9917be8cd1b399219
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08198449B2

Reaction notes

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