Ethanolamine → N-(2-hydroxy-ethyl)-2-[2-(4-trifluoromethyl-phenoxymethyl)-1H-benzoimidazol-5-yl]-benzamide

HRID 1433220Notes

Reaction equation

HRID 1433220 reaction equation
[F:1][C:2]([F:30])([F:29])[C:3]1[CH:28]=[CH:27][C:6]([O:7][CH2:8][C:9]2[NH:13][C:12]3[CH:14]=[CH:15][C:16]([C:18]4[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=4[C:20](O)=[O:21])=[CH:17][C:11]=3[N:10]=2)=[CH:5][CH:4]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.CCN(C(C)C)C(C)C.[CH2:67]([CH2:69][NH2:70])[OH:68]>CN(C=O)C>[OH:68][CH2:67][CH2:69][NH:70][C:20](=[O:21])[C:19]1[CH:23]=[CH:24][CH:25]=[CH:26][C:18]=1[C:16]1[CH:15]=[CH:14][C:12]2[NH:13][C:9]([CH2:8][O:7][C:6]3[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:29])[F:30])=[CH:28][CH:27]=3)=[N:10][C:11]=2[CH:17]=1

Participants

6

Reactant 4

HCID 700EthanolamineHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 1785242792-[2-(4-trifluoromethyl-phenoxymethyl)-1H-benzoimidazol-5-yl]-benzoic acid

Product 1

HCID 178523439N-(2-hydroxy-ethyl)-2-[2-(4-trifluoromethyl-phenoxymethyl)-1H-benzoimidazol-5-yl]-benzamideYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-[2-(4-trifluoromethyl-phenoxymethyl)-1H-benzoimidazol-5-yl]-benzoic acid (0.050 g, 0.121 mmol), BOP (0.059 g, 0.133 mmol), DIPEA (0.07 mL, 0.363 mmol) and ethanolamine (0.011 g, 0.182 mmol) in DMF (0.5 mL) was stirred at rt for 12 hours. The crude product was purified by chromatography (silica, CH2Cl2: MeOH, 5:1) to afford the title compound as a brown oil (0.043 g, 78%). 1H NMR (400 MHz, CD3OD) δ (ppm): 7.64-7.59 (m, 3H), 7.54-7.46 (m, 4H), 7.41 (td, 1H, J=8.2 Hz, J=1.6 Hz), 7.35 (dd, 1H, J=8.0 Hz, J=1.6 Hz), 7.15 (d, 2H, J=8.0 Hz), 5.42 (s, 2H), 5.24 (s, 1H), 3.91 (t, 2H, J=6.0 Hz), 3.24 (t, 2H, J=6.2 Hz). Mass Spectrum (LCMS, ESI pos.) Calcd. For C24H21F3N3O3: 456.4 (M+H), Found 456.2.

Workup

  1. customThe crude product was purified by chromatography (silica, CH2Cl2: MeOH, 5:1)

Sources & evidence

ORD record
ord-c7b94cf407ab4d61b5dd56dbd8d9228a
Source dataset
uspto-grants-2009_11
Patent number
US07612211B2

Reaction notes

Loading…