1-(4-Fluorophenyl)cyclopropan-1-amine hydrochloride → Ammonium Acetate

HRID 44037Notes

Reaction equation

[CH2:1]([N:3]([C:8]1[C:9]([C:28]2[CH:29]=[C:30]([CH:34]=[CH:35][C:36]=2[CH3:37])[C:31]([OH:33])=[O:32])=[CH:10][C:11]2[N:12]([N:14]=[C:15]([C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)[C:16]=2[C:17](=[O:20])[NH:18][CH3:19])[CH:13]=1)[S:4]([CH3:7])(=[O:6])=[O:5])[CH3:2].Cl.[F:39][C:40]1[CH:45]=[CH:44][C:43]([C:46]2([NH2:49])[CH2:48][CH2:47]2)=[CH:42][CH:41]=1>>[C:31]([O-:33])(=[O:32])[CH3:30].[NH4+:3].[CH2:1]([N:3]([C:8]1[C:9]([C:28]2[CH:29]=[C:30]([C:31](=[O:32])[NH:49][C:46]3([C:43]4[CH:44]=[CH:45][C:40]([F:39])=[CH:41][CH:42]=4)[CH2:48][CH2:47]3)[CH:34]=[CH:35][C:36]=2[CH3:37])=[CH:10][C:11]2[N:12]([N:14]=[C:15]([C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)[C:16]=2[C:17]([NH:18][CH3:19])=[O:20])[CH:13]=1)[S:4]([CH3:7])(=[O:5])=[O:6])[CH3:2]

Participants

Reactant 2

HCID 242065851-(4-Fluorophenyl)cyclopropan-1-amine hydrochloride

HCID 67217751HCID 67217751, compound

Product 2

HCID 517165Ammonium Acetate

HCID 592336616-(N-ethylmethylsulfonamido)-2-(4-fluorophenyl)-5-(5-(1-(4-fluorophenyl)cyclopropylcarbamoyl)-2-methylphenyl)-N-methylpyrazolo[1,5-a]pyridine-3-carboxamide

Procedure

6-(N-ethylmethylsulfonamido)-2-(4-fluorophenyl)-5-(5-(1-(4-fluorophenyl)cyclopropylcarbamoyl)-2-methylphenyl)-N-methylpyrazolo[1,5-a]pyridine-3-carboxamide was prepared from 3-(6-(N-ethylmethylsulfonamido)-2-(4-fluorophenyl)-3-(methylcarbamoyl)pyrazolo[1,5-a]pyridin-5-yl)-4-methylbenzoic acid (0.024 g, 0.046 mmol) and 1-(4-fluorophenyl)cyclopropanamine hydrochloride (0.013 g, 0.069 mmol). The resultant residue was purified using preparative HPLC (Waters—Xbridge, 50×100 mm, 5 micron, C18 column; 0.1M ammonium acetate, 10-100% B (B=5% H2O/CH3CN)/A (A=95% H2O/CH3CN), 15 min. gradient) to afford 6-(N-ethylmethylsulfonamido)-2-(4-fluorophenyl)-5-(5-(1-(4-fluorophenyl)cyclopropylcarbamoyl)-2-methylphenyl)-N-methylpyrazolo[1,5-a]pyridine-3-carboxamide as a white solid. Preparative HPLC retention time: 8.5 min. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 8.54 (s, 1H), 8.29 (s, 1H), 7.82 (br. s., 2H), 7.65-7.77 (m, 2H), 7.40 (d, J=7.78 Hz, 2H), 7.31-7.38 (m, 3H), 7.22-7.30 (m, 4H), 6.90-7.00 (m, 2H), 5.55 (d, J=4.77 Hz, 1H), 3.42 (br. s., 1H), 3.00-3.12 (m, 2H), 2.78-2.90 (m, 4H), 2.34 (s, 3H), 1.62 (br. s., 2H), 1.25-1.37 (m, 5H), 1.08 (br. s., 3H). LCMS retention time: 1.920 min. LC data was recorded on a Shimadzu LC-10AS liquid chromatograph equipped with a Phenomenex-Luna, 10 micron, C18, 3.0×50 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 5% CH3CN/95% H2O/10 mM ammonium acetate and solvent B was 5% H2O/95% CH3CN/10 mM ammonium acetate. MS data was determined using a Micromass Platform for LC in electrospray mode. m/z 658 (MH+).

Workup

customThe resultant residue was purified

Sources & evidence

ORD record: ord-6519899e854f4dafb019d0ce75f6e58e
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08536338B2

Reaction notes

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