Diisopropylethylamine → 3-(4-methyl-imidazol-1-yl)-N-{3-[3-(2-oxo-2,3-dihydro-1H-indol-6-yl)-ureido]-phenyl}-5-trifluoromethyl-benzamide

HRID 422012Notes

Reaction equation

HRID 422012 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]([NH:11][C:12]2[CH:20]=[C:19]3[C:15]([CH2:16][C:17](=[O:21])[NH:18]3)=[CH:14][CH:13]=2)=[O:10])[CH:5]=[CH:6][CH:7]=1.[CH3:22][C:23]1[N:24]=[CH:25][N:26]([C:28]2[CH:29]=[C:30]([CH:34]=[C:35]([C:37]([F:40])([F:39])[F:38])[CH:36]=2)[C:31](O)=[O:32])[CH:27]=1.C(N(CC)C(C)C)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[CH3:22][C:23]1[N:24]=[CH:25][N:26]([C:28]2[CH:29]=[C:30]([CH:34]=[C:35]([C:37]([F:40])([F:38])[F:39])[CH:36]=2)[C:31]([NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([NH:8][C:9]([NH:11][C:12]3[CH:20]=[C:19]4[C:15]([CH2:16][C:17](=[O:21])[NH:18]4)=[CH:14][CH:13]=3)=[O:10])[CH:3]=2)=[O:32])[CH:27]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 469002413-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)benzoic acidHCID 59804327HCID 59804327, compound

Product 1

HCID 598043033-(4-methyl-imidazol-1-yl)-N-{3-[3-(2-oxo-2,3-dihydro-1H-indol-6-yl)-ureido]-phenyl}-5-trifluoromethyl-benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-(3-amino-phenyl)-3-(2-oxo-2,3-dihydro-1H-indol-6-yl)-urea (75 mg, 0.27 mmol) is dissolved in DMF (5 ml). To this solution is added 3-(4-methyl-imidazol-1-yl)-5-trifluoromethyl-benzoic acid (73 mg, 0.27 mmol), N,N-diisopropylethylamine (105 mg, 0.81 mmol) and HATU (0.10 g, 0.26 mmol). It is stirred for 24 hours and then concentrated. 3-(4-methyl-imidazol-1-yl)-N-{3-[3-(2-oxo-2,3-dihydro-1H-indol-6-yl)-ureido]-phenyl}-5-trifluoromethyl-benzamide is obtained after HPLC purification. LC-MS: 535.2 (MH+).

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-4d7b740df2a24e6ab3d4e1708d0e86fc
Source dataset
uspto-grants-2012_01
Patent number
US08101608B2

Reaction notes

Loading…