1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 57387078, compound

HRID 2190514Notes

Reaction equation

HRID 2190514 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][CH:24]=1)[O:5][C:6]1[CH:7]=[CH:8][C:9]2[N:13]=[C:12]([NH:14][C:15]([CH:17]3[CH2:19][CH2:18]3)=[O:16])[N:11]([CH3:20])[C:10]=2[CH:21]=1.[C:25]([C:27]([C:30]1[CH:31]=[C:32]([CH:36]=[CH:37][CH:38]=1)[C:33](O)=[O:34])([CH3:29])[CH3:28])#[N:26].Cl.C(N=C=NCCCN(C)C)C>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[C:25]([C:27]([C:30]1[CH:31]=[C:32]([CH:36]=[CH:37][CH:38]=1)[C:33]([NH:1][C:2]1[CH:24]=[CH:23][CH:22]=[C:4]([O:5][C:6]2[CH:7]=[CH:8][C:9]3[N:13]=[C:12]([NH:14][C:15]([CH:17]4[CH2:19][CH2:18]4)=[O:16])[N:11]([CH3:20])[C:10]=3[CH:21]=2)[CH:3]=1)=[O:34])([CH3:29])[CH3:28])#[N:26]

Participants

6

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 571495383-(2-Cyanopropan-2-yl)benzoic acidHCID 57388052HCID 57388052, compound

Product 1

HCID 57387078HCID 57387078, compoundYield 38.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

Using N-[6-(3-aminophenoxy)-1-methyl-1H-benzimidazol-2-yl]cyclopropanecarboxamide (166 mg, 514.3 μmol) produced in Example C4(vi), 3-(1-cyano-1-methylethyl)benzoic acid (316 mg, 1.67 mmol), pyridine (5 mL), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (456 mg, 2.38 mmol) and N,N-dimethylpyridine-4-amine (38.9 mg, 318 μmol) as starting materials, and in the same manner as in Example C4(vii), the title compound (97.3 mg, 38%) was obtained as colorless crystals.

Sources & evidence

ORD record
ord-6aece38719404d05aa5eef3f1de8da53
Source dataset
uspto-grants-2012_12
Patent number
US08324395B2

Reaction notes

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