1-Hydroxybenzotriazole → HCID 86648849, compound

HRID 1425437Notes

Reaction equation

HRID 1425437 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:9]=[CH:10][C:11]([O:18][CH3:19])=[C:12]([CH:17]=2)[C:13]([O:15][CH3:16])=[O:14])[CH2:4][C@H:3]1[O:20][CH3:21].[Cl:22][C:23]1[N:24]=[C:25]([C:30](O)=[O:31])[NH:26][C:27]=1[CH2:28][CH3:29].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>CC(N(C)C)=O.ClCCl>[Cl:22][C:23]1[N:24]=[C:25]([C:30]([NH:1][C@H:2]2[CH2:7][CH2:6][N:5]([C:8]3[CH:9]=[CH:10][C:11]([O:18][CH3:19])=[C:12]([CH:17]=3)[C:13]([O:15][CH3:16])=[O:14])[CH2:4][C@H:3]2[O:20][CH3:21])=[O:31])[NH:26][C:27]=1[CH2:28][CH3:29]

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 675489294-chloro-5-ethyl-1H-imidazole-2-carboxylic acidHCID 86648848Methyl cis(+/-)-5-(4-amino-3-methoxypiperidin-1-yl)-2-methoxybenzoate

Product 1

HCID 86648849HCID 86648849, compoundYield 58.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 31374DimethylacetamideSolvent

Procedure

The same operation as in Example (1g) was performed using methyl cis(±)-5-(4-amino-3-methoxypiperidin-1-yl)-2-methoxybenzoate obtained in Example (258b) (about 0.08 mmol), 4-chloro-5-ethyl-1H-imidazole-2-carboxylic acid obtained in Example (1d) (14 mg, 0.08 mmol), WSC hydrochloride (52 mg, 0.27 mmol), HOBT (18 mg, 0.14 mmol), dichloromethane (1 mL) and DMA (1 mL), to obtain 21 mg of the title compound as a colorless oily substance (57%).

Sources & evidence

ORD record
ord-66352e77756d412092ab138a876eab50
Source dataset
uspto-grants-2015_01
Patent number
US08927588B2

Reaction notes

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