Triethylamine → 4-(3-(Cyclopropylmethyl)ureido)-N-(1-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)benzyl)piperidin-4-yl)-N-methylbenzamide

HRID 515327Notes

Reaction equation

HRID 515327 reaction equation
[CH:1]1([CH2:4][NH:5][C:6](=[O:17])[NH:7][C:8]2[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][CH:9]=2)[CH2:3][CH2:2]1.[F:18][C:19]([F:42])([F:41])[C:20]([C:26]1[CH:31]=[CH:30][C:29]([CH2:32][N:33]2[CH2:38][CH2:37][CH:36]([NH:39][CH3:40])[CH2:35][CH2:34]2)=[CH:28][CH:27]=1)([OH:25])[C:21]([F:24])([F:23])[F:22].C(N(CC)CC)C.Cl.C(N=C=NCCCN(C)C)C>ClCCl.ClCCl.CO>[CH:1]1([CH2:4][NH:5][C:6](=[O:17])[NH:7][C:8]2[CH:9]=[CH:10][C:11]([C:12]([N:39]([CH:36]3[CH2:37][CH2:38][N:33]([CH2:32][C:29]4[CH:28]=[CH:27][C:26]([C:20]([OH:25])([C:19]([F:42])([F:18])[F:41])[C:21]([F:22])([F:23])[F:24])=[CH:31][CH:30]=4)[CH2:34][CH2:35]3)[CH3:40])=[O:14])=[CH:15][CH:16]=2)[CH2:2][CH2:3]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 580558194-(3-(Cyclopropylmethyl)ureido)benzoic acidHCID 866709591,1,1,3,3,3-Hexafluoro-2-(4-((4-(methylamino)piperidin-1-yl)methyl)phenyl)propan-2-ol

Product 1

HCID 866709614-(3-(Cyclopropylmethyl)ureido)-N-(1-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)benzyl)piperidin-4-yl)-N-methylbenzamideYield 77.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 21226129Dichloromethane methanolSolvent

Procedure

To a mixture of 4-(3-(cyclopropylmethyl)ureido)benzoic acid (0.810 mmol, 190 mg), 1,1,1,3,3,3-hexafluoro-2-(4-((4-(methylamino)piperidin-1-yl)methyl)phenyl)propan-2-ol (0.810 mmol, 300 mg) and triethylamine (1.944 mmol, 0.271 mL, 197 mg) in dichloromethane (50 mL) was added N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (0.972 mmol, 186 mg). The reaction was stirred for 24 hours. Chromatography on silica eluting with dichloromethane to dichloromethane/methanol (10%) gave the title compound (370 mg).

Sources & evidence

ORD record
ord-fc1d828f8338496cac17239901602189
Source dataset
uspto-grants-2015_08
Patent number
US09108939B2

Reaction notes

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