Triethylamine → HCID 86670964, compound

HRID 515330Notes

Reaction equation

HRID 515330 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.[CH2:18]([NH:20][CH:21]1[CH2:26][CH2:25][N:24]([CH2:27][C:28]2[CH:33]=[CH:32][C:31]([C:34]([OH:43])([C:39]([F:42])([F:41])[F:40])[C:35]([F:38])([F:37])[F:36])=[CH:30][CH:29]=2)[CH2:23][CH2:22]1)[CH3:19].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:20]([CH2:18][CH3:19])[CH:21]3[CH2:26][CH2:25][N:24]([CH2:27][C:28]4[CH:29]=[CH:30][C:31]([C:34]([OH:43])([C:35]([F:38])([F:36])[F:37])[C:39]([F:40])([F:41])[F:42])=[CH:32][CH:33]=4)[CH2:23][CH2:22]3)=[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 86670962HCID 86670962, compound

Product 1

HCID 86670964HCID 86670964, compoundYield 53.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 21226129Dichloromethane methanolSolvent

Procedure

To a mixture of 4-(3-(cyclopropylmethyl)ureido)benzoic acid (0.781 mmol, 183 mg), 2-(4-((4-(ethylamino)piperidin-1-yl)methyl)phenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (0.781 mmol, 300 mg) and triethylamine (1.873 mmol, 0.261 mL, 190 mg) in dichloromethane (50 mL) was added N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (0.937 mmol, 180 mg). The reaction was stirred for 24 hours. Chromatography on silica eluting with dichloromethane to dichloromethane/methanol (10%) gave the title compound (250 mg).

Sources & evidence

ORD record
ord-901ab4ee21a549f89148a1fccdb028e3
Source dataset
uspto-grants-2015_08
Patent number
US09108939B2

Reaction notes

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