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

HRID 44038Notes

Reaction equation

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

Participants

Reactant 2

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

HCID 672176903-(2-(4-Fluorophenyl)-3-(methylcarbamoyl)pyrazolo[1,5-a]pyridin-5-yl)-4-methylbenzoic acid

Product 2

HCID 517165Ammonium Acetate

HCID 59233768HCID 59233768, compound

Procedure

2-(4-fluorophenyl)-5-(5-(1-(4-fluorophenyl)cyclopropylcarbamoyl)-2-methylphenyl)-N-methylpyrazolo[1,5-a]pyridine-3-carboxamide was prepared from 3-(2-(4-fluorophenyl)-3-(methylcarbamoyl)pyrazolo[1,5-a]pyridin-5-yl)-4-methylbenzoic acid (0.016 g, 0.040 mmol) and 1-(4-fluorophenyl)cyclopropanamine hydrochloride (0.011 g, 0.059 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 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: 10.5 min. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.24 (s, 1H), 8.84 (d, J=7.03 Hz, 1H), 7.83-7.96 (m, 5H), 7.75 (s, 1H), 7.47 (d, J=8.03 Hz, 1H), 7.26-7.38 (m, 4H), 7.05-7.16 (m, 3H), 2.78 (d, J=4.77 Hz, 3H), 2.37 (s, 3H), 1.26 (d, J=6.27 Hz, 4H). LCMS retention time: 2.533 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 10% methanol/90% water/10 mM TFA and solvent B was 10% water/90% methanol/10 mM TFA. MS data was determined using a Micromass Platform for LC in electrospray mode. m/z 537 (MH+).

Workup

customThe resultant residue was purified

Sources & evidence

ORD record: ord-f79673b5fe184b15a6d884c09ff799df
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08536338B2

Reaction notes

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