Methylamine → 5-(4-chloro-1-methyl-1H-pyrazol-5-yl)-2-[(1S)-1-(3-fluorobenzyl)-2-(methylamino)ethyl]isoindolin-1-one

HRID 339969Notes

Reaction equation

HRID 339969 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][N:5]([CH3:28])[C:6]=1[C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[C:12](=[O:16])[N:11]([C@@H:17]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[CH:22]=1)[CH:18]=O)[CH2:10]2.[CH3:29][NH2:30].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>O1CCCC1>[Cl:1][C:2]1[CH:3]=[N:4][N:5]([CH3:28])[C:6]=1[C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[C:12](=[O:16])[N:11]([C@@H:17]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[CH:22]=1)[CH2:18][NH:30][CH3:29])[CH2:10]2

Participants

5

Reactant 3

HCID 6329MethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 86681462(2S)-2-[5-(4-chloro-1-methyl-1H-pyrazol-5-yl)-1-oxo-1,3-dihydro-2H-isoindol-2-yl]-3-(3-fluorophenyl)propanal

Product 1

HCID 715557735-(4-chloro-1-methyl-1H-pyrazol-5-yl)-2-[(1S)-1-(3-fluorobenzyl)-2-(methylamino)ethyl]isoindolin-1-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (2S)-2-[5-(4-chloro-1-methyl-1H-pyrazol-5-yl)-1-oxo-1,3-dihydro-2H-isoindol-2-yl]-3-(3-fluorophenyl)propanal (40.0 mg, 0.100 mmol), methylamine (20.3 μL, 0.151 mmol) and sodium triacetoxyborohydride (42.6 mg, 0.201 mmol) in tetrahydrofuran (1 mL) was stirred at room temperature overnight. Direct purification on prep.—HPLC (pH=10) gave the desired product as white solid. LC-MS found: 413.1 (M+H)+.

Workup

  1. customDirect purification on prep.—HPLC (pH=10)

Sources & evidence

ORD record
ord-33703fb53c274c5599ce5f53b6de6f0c
Source dataset
uspto-grants-2014_11
Patent number
US08895571B2

Reaction notes

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