1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 58349027, compound

HRID 2190507Notes

Reaction equation

HRID 2190507 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]1([C:29]2[CH:30]=[C:31]([CH:35]=[CH:36][CH:37]=2)[C:32](O)=[O:33])[CH2:28][CH2:27]1)#[N:25].Cl.C(N=C=NCCCN(C)C)C>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[C:24]([C:26]1([C:29]2[CH:30]=[C:31]([CH:35]=[CH:36][CH:37]=2)[C:32]([NH:1][C:2]2[CH:23]=[CH:22][CH:21]=[C:4]([O:5][C:6]3[CH:7]=[CH:8][C:9]4[N:13]=[C:12]([NH:14][C:15]([CH:17]5[CH2:19][CH2:18]5)=[O:16])[NH:11][C:10]=4[CH:20]=3)[CH:3]=2)=[O:33])[CH2:27][CH2:28]1)#[N:25]

Participants

6

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57388051N-[6-(3-aminophenoxy)-1H-benzimidazol-2-yl]cyclopropanecarboxamideHCID 574410393-(1-Cyanocyclopropyl)benzoic acid

Product 1

HCID 58349027HCID 58349027, compoundYield 43.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

Using N-[6-(3-aminophenoxy)-1H-benzimidazol-2-yl]cyclopropanecarboxamide (159 mg, 515 μmol) produced in Example C1(vi), 3-(1-cyanocyclopropyl)benzoic acid (210 mg, 1.12 mmol), pyridine (5 mL), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (307 mg, 1.60 mmol) and N,N-dimethylpyridine-4-amine (58.1 mg, 47.6 μmol) as starting materials, and in the same manner as in Example C1(vii), the title compound (107 mg, 43%) was obtained as colorless crystals.

Sources & evidence

ORD record
ord-923a734902984185bc4214a517882650
Source dataset
uspto-grants-2012_12
Patent number
US08324395B2

Reaction notes

Loading…