1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 67288339, compound

HRID 1626446Notes

Reaction equation

HRID 1626446 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH2:9][CH2:10][NH2:11])=[CH:7][CH:6]=[C:5]([C:12]([F:15])([F:14])[F:13])[N:4]=1.[Cl:16][C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][C:26]=1[O:27][C:28]1[CH:36]=[CH:35][C:31]([C:32](O)=[O:33])=[CH:30][CH:29]=1)[O:23][CH2:22][CH2:21][CH:20]2[C:37]([O:39][CH2:40][CH3:41])=[O:38].Cl.C(N=C=NCCCN(C)C)C>ClCCl.CN(C)C1C=CN=CC=1>[Cl:16][C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][C:26]=1[O:27][C:28]1[CH:36]=[CH:35][C:31]([C:32](=[O:33])[NH:11][CH2:10][CH2:9][C:8]3[C:3]([O:2][CH3:1])=[N:4][C:5]([C:12]([F:15])([F:14])[F:13])=[CH:6][CH:7]=3)=[CH:30][CH:29]=1)[O:23][CH2:22][CH2:21][CH:20]2[C:37]([O:39][CH2:40][CH3:41])=[O:38]

Participants

6

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 582443954-(6-Chloro-4-(ethoxycarbonyl)chroman-7-yloxy)benzoic acidHCID 67287344HCID 67287344, compound

Product 1

HCID 67288339HCID 67288339, compoundYield 71.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

2-(2-Methoxy-6-(trifluoromethyl)pyridin-3-yl)ethanamine (140 mg, 0.637 mmol) in dichloromethane (1 ml) was treated sequentially with 4-(6-chloro-4-(ethoxycarbonyl)chroman-7-yloxy)benzoic acid (Preparation B; 240 mg, 0.637 mmol), N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (147 mg, 0.764 mmol), and 4-(dimethylamino)pyridine (7.78 mg, 0.0637 mmol) at ambient temperature. After 14 hours, the reaction was applied directly to silica gel. Elution with ethyl acetate (50-80%) provided the desired compound (264 mg, 0.456 mmol, 71.6% yield) as a white solid.

Workup

  1. washElution with ethyl acetate (50-80%)

Sources & evidence

ORD record
ord-d85f4c495d4c4e47a146238fbca4aa74
Source dataset
uspto-grants-2014_07
Patent number
US08785445B2

Reaction notes

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