Glycolaldehyde dimer → 2-(6-Chloro-benzothiazol-2-ylamino)-1-(2-methoxy-ethyl)-1H-benzoimidazole-5-carboxylic acid [1-(2-hydroxy-ethyl)-piperidin-4-ylmethyl]-amide

HRID 411029Notes

Reaction equation

HRID 411029 reaction equation
Cl.Cl.[NH:3]1[CH2:8][CH2:7][CH:6]([CH2:9][NH:10][C:11]([C:13]2[CH:36]=[CH:35][C:16]3[N:17]([CH2:31][CH2:32][O:33][CH3:34])[C:18]([NH:20][C:21]4[S:22][C:23]5[CH:29]=[C:28]([Cl:30])[CH:27]=[CH:26][C:24]=5[N:25]=4)=[N:19][C:15]=3[CH:14]=2)=[O:12])[CH2:5][CH2:4]1.[O:37]1CC(O)O[CH2:39][CH:38]1O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[OH:37][CH2:38][CH2:39][N:3]1[CH2:8][CH2:7][CH:6]([CH2:9][NH:10][C:11]([C:13]2[CH:36]=[CH:35][C:16]3[N:17]([CH2:31][CH2:32][O:33][CH3:34])[C:18]([NH:20][C:21]4[S:22][C:23]5[CH:29]=[C:28]([Cl:30])[CH:27]=[CH:26][C:24]=5[N:25]=4)=[N:19][C:15]=3[CH:14]=2)=[O:12])[CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 186078Glycolaldehyde dimerHCID 5049666Sodium triacetoxyborohydrideHCID 866569502-(6-Chloro-benzothiazol-2-ylamino)-1-(2-methoxy-ethyl)-1H-benzoimidazole-5-carboxylic acid (piperidin-4-ylmethyl)-amide dihydrochloride

Product 1

HCID 866569522-(6-Chloro-benzothiazol-2-ylamino)-1-(2-methoxy-ethyl)-1H-benzoimidazole-5-carboxylic acid [1-(2-hydroxy-ethyl)-piperidin-4-ylmethyl]-amideYield 34.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(6-Chloro-benzothiazol-2-ylamino)-1-(2-methoxy-ethyl)-1H-benzoimidazole-5-carboxylic acid [1-(2-hydroxy-ethyl)piperidin-4-ylmethyl]-amide (45 mg) was prepared by following General Procedure P starting from 2-(6-chloro-benzothiazol-2-ylamino)-1-(2-methoxy-ethyl)-1H-benzoimidazole-5-carboxylic acid (piperidin-4-ylmethyl)-amide dihydrochloride (136 mg), [1,4]dioxane-2,5-diol (54 mg), and Na(OAc)3BH (95 mg) in DCM (2 mL). LC/MS: m/z 542.7.

Sources & evidence

ORD record
ord-82109f2b565f4713b32056c54a31a838
Source dataset
uspto-grants-2014_06
Patent number
US08759535B2

Reaction notes

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