N-Methylbenzylamine → HCID 59275306, compound

HRID 555091Notes

Reaction equation

HRID 555091 reaction equation
CCN(C(C)C)C(C)C.[CH3:10][NH:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[F:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[O:27][C:28]3[CH:38]=[CH:37][C:36]([C:39]4[CH:40]=[C:41]([CH:45]=[CH:46][CH:47]=4)[C:42](O)=[O:43])=[CH:35][C:29]=3[C:30]=2[C:31](=[O:34])[NH:32][CH3:33])=[CH:22][CH:21]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.CO>[CH2:12]([N:11]([CH3:10])[C:42]([C:41]1[CH:40]=[C:39]([C:36]2[CH:37]=[CH:38][C:28]3[O:27][C:26]([C:23]4[CH:24]=[CH:25][C:20]([F:19])=[CH:21][CH:22]=4)=[C:30]([C:31]([NH:32][CH3:33])=[O:34])[C:29]=3[CH:35]=2)[CH:47]=[CH:46][CH:45]=1)=[O:43])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 7669N-MethylbenzylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 592754243-[2-(4-Fluorophenyl)-3-(methylcarbamoyl)-1-benzofuran-5-yl]benzoic acid

Product 1

HCID 59275306HCID 59275306, compoundYield 47.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

DIPEA (50 μL, 0.29 mmol) and N-methylbenzylamine (20 μL, 0.16 mmol) were added to a stirred suspension of 3-(2-(4-fluorophenyl)-3-(methylcarbamoyl)benzofuran-5-yl)benzoic acid (20 mg, 0.051 mmol) and HATU (25 mg, 0.066 mmol) in DMF (0.5 mL) and the reaction was stirred at r.t. overnight. The reaction was then diluted with MeOH, filtered, purified by prep HPLC, and concentrated to give the title compound as a tan powder (12 mg, 47% yield). 1H NMR (500 MHz, DMSO-d6) δ ppm 8.50 (br. s., 1H) 8.01 (dd, J=8.39, 5.65 Hz, 2H) 7.66-7.93 (m, 5H) 7.58 (br. s., 1H) 7.42-7.50 (m, 1H) 7.35-7.42 (m, 4H) 7.31 (d, J=5.80 Hz, 1H) 7.23 (d, J=4.58 Hz, 1H) 4.72 (br. s., 1H) 4.54 (br. s., 1H) 2.83-3.00 (m, 6H). LC/MS was performed by using Shimadzu-VP instrument with UV detection at 220 nm and Waters MICROMASS®. LC/MS method: solvent A=10% CH3CN/90% H2O/0.1% TFA, solvent B=90% CH3CN/10% H2O/0.1% TFA, start % B=0, final % B=100, gradient time=2 min, stop time=3 min, flow rate=4 ml/min, column: Sunfire C18 5 μm 4.6×50 mm; HPLC Rt=1.85 min, (ES+) m/z (MH+)=493. Analytical HPLC method: solvent A=5% CH3CN/95% H2O/0.1% TFA, solvent B=95% CH3CN/5% H2O/0.1% TFA, start % B=10, final % B=100, gradient time=15 min, stop time=18 min, flow rate=1 ml/min. Column: Waters Sunfire C-18, 3.5 μm 4.6×150 mm, Rt=16.26 min, purity=99%; column: Waters XBridge phenyl 3.5 μm 4.6×150 mm, Rt=12.81 min, purity=98%.

Workup

  1. filtrationfiltered
  2. custompurified by prep HPLC
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-a27e0d0f738d4be388e61ab7d41df482
Source dataset
uspto-grants-2011_11
Patent number
US08048887B2

Reaction notes

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