Triethylamine → 1-(4-{7-[4-(4-Methyl-piperazine-1-carbonyl)-phenyl]-imidazo[1,2-a]pyridin-3-yl}-benzyl)-3-(3-trifluoromethyl-phenyl)-urea

HRID 1446770Notes

Reaction equation

HRID 1446770 reaction equation
Cl.Cl.[NH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:15]3[CH:16]=[CH:17][C:18]([C:20]4[CH:25]=[CH:24][C:23]([C:26]([N:28]5[CH2:33][CH2:32][N:31]([CH3:34])[CH2:30][CH2:29]5)=[O:27])=[CH:22][CH:21]=4)=[CH:19][C:14]3=[N:13][CH:12]=2)=[CH:7][CH:6]=1.[F:35][C:36]([F:47])([F:46])[C:37]1[CH:38]=[C:39]([N:43]=[C:44]=[O:45])[CH:40]=[CH:41][CH:42]=1.C(N(CC)CC)C>CS(C)=O>[CH3:34][N:31]1[CH2:32][CH2:33][N:28]([C:26]([C:23]2[CH:22]=[CH:21][C:20]([C:18]3[CH:17]=[CH:16][N:15]4[C:11]([C:8]5[CH:7]=[CH:6][C:5]([CH2:4][NH:3][C:44]([NH:43][C:39]6[CH:40]=[CH:41][CH:42]=[C:37]([C:36]([F:35])([F:46])[F:47])[CH:38]=6)=[O:45])=[CH:10][CH:9]=5)=[CH:12][N:13]=[C:14]4[CH:19]=3)=[CH:25][CH:24]=2)=[O:27])[CH2:29][CH2:30]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 94833-(Trifluoromethyl)phenyl isocyanateHCID 131727906{4-[3-(4-Aminomethyl-phenyl)-imidazo[1,2-a]pyridin-7-yl]-phenyl}-(4-methyl-piperazin-1-yl)-methanone, bis hydrochloride

Product 1

HCID 578634251-(4-{7-[4-(4-Methyl-piperazine-1-carbonyl)-phenyl]-imidazo[1,2-a]pyridin-3-yl}-benzyl)-3-(3-trifluoromethyl-phenyl)-ureaYield 52.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Combine {4-[3-(4-aminomethyl-phenyl)-imidazo[1,2-a]pyridin-7-yl]-phenyl}-(4-methyl-piperazin-1-yl)-methanone, bis hydrochloride (0.30 g, 0.56 mmol), 3-trifluoromethylphenyl isocyanate (0.1 mL, 0.73 mmol) and triethylamine (0.4 mL, 2.9 mmol) in DMSO (10 mL). Filter the solution through 10 g SCX column eluting with methanol→2 N ammonia in methanol. Concentrate fractions containing product to give a residue. Purify by chromatography (5% methanol in dichloromethane→10% methanol in dichloromethane→10% 2 N ammonia methanol in dichloromethane) to afford product (0.18 g, 52%). MS(ES), m/z 613 (M+1).

Workup

  1. filtrationFilter the solution through 10 g SCX column
  2. washeluting with methanol→2 N ammonia in methanol
  3. additionConcentrate fractions containing product
  4. customto give a residue
  5. customPurify by chromatography (5% methanol in dichloromethane→10% methanol in dichloromethane→10% 2 N ammonia methanol in dichloromethane)

Sources & evidence

ORD record
ord-1e8a202254f64b1d8a30f69b9ea9605b
Source dataset
uspto-grants-2010_02
Patent number
US07666879B2

Reaction notes

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