1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 57387077, compound

HRID 2190504Notes

Reaction equation

HRID 2190504 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=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])[NH:11][C:10]=2[CH:20]=1.[C:24]([C:26]([C:29]1[CH:30]=[C:31]([CH:35]=[CH:36][CH:37]=1)[C:32](O)=[O:33])([CH3:28])[CH3:27])#[N:25].Cl.C(N=C=NCCCN(C)C)C>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[C:24]([C:26]([C:29]1[CH:30]=[C:31]([CH:35]=[CH:36][CH:37]=1)[C:32]([NH:1][C:2]1[CH:23]=[CH:22][CH:21]=[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])[NH:11][C:10]=3[CH:20]=2)[CH:3]=1)=[O:33])([CH3:28])[CH3:27])#[N:25]

Participants

6

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 571495383-(2-Cyanopropan-2-yl)benzoic acidHCID 57388051N-[6-(3-aminophenoxy)-1H-benzimidazol-2-yl]cyclopropanecarboxamide

Product 1

HCID 57387077HCID 57387077, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

Using N-[6-(3-aminophenoxy)-1H-benzimidazol-2-yl]cyclopropanecarboxamide (156 mg, 506 mmol) produced in Example C1(vi), 3-(1-cyano-1-methylethyl)benzoic acid (195 mg, 1.03 mmol), pyridine (5 mL), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (407 mg, 2.12 mmol) and N,N-dimethylpyridine-4-amine (58.2 mg, 476 μmol) as starting materials, and in the same manner as in Example C1(vii), the title compound (168 mg, 69%) was obtained as colorless crystals.

Sources & evidence

ORD record
ord-7a632276cd5c49539163b5ed47836ab5
Source dataset
uspto-grants-2012_12
Patent number
US08324395B2

Reaction notes

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