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

HRID 411023Notes

Reaction equation

HRID 411023 reaction equation
Cl.Cl.[NH:3]1[CH2:8][CH2:7][CH:6]([NH:9][C:10]([C:12]2[CH:35]=[CH:34][C:15]3[N:16]([CH2:30][CH2:31][O:32][CH3:33])[C:17]([NH:19][C:20]4[S:21][C:22]5[CH:28]=[C:27]([Cl:29])[CH:26]=[CH:25][C:23]=5[N:24]=4)=[N:18][C:14]=3[CH:13]=2)=[O:11])[CH2:5][CH2:4]1.[O:36]1CC(O)O[CH2:38][CH:37]1O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[OH:36][CH2:37][CH2:38][N:3]1[CH2:4][CH2:5][CH:6]([NH:9][C:10]([C:12]2[CH:35]=[CH:34][C:15]3[N:16]([CH2:30][CH2:31][O:32][CH3:33])[C:17]([NH:19][C:20]4[S:21][C:22]5[CH:28]=[C:27]([Cl:29])[CH:26]=[CH:25][C:23]=5[N:24]=4)=[N:18][C:14]=3[CH:13]=2)=[O:11])[CH2:7][CH2:8]1

Participants

5

Reactant 3

HCID 186078Glycolaldehyde dimerHCID 5049666Sodium triacetoxyborohydrideHCID 866569422-(6-Chloro-benzothiazol-2-ylamino)-1-(2-methoxy-ethyl)-1H-benzoimidazole-5-carboxylic acid piperidin-4-ylamide dihydrochloride

Product 1

HCID 866569442-(6-Chloro-benzothiazol-2-ylamino)-1-(2-methoxy-ethyl)-1H-benzoimidazole-5-carboxylic acid [1-(2-hydroxy-ethyl)-piperidin-4-yl]-amideYield 37.8%

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-yl]-amide (52 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-ylamide dihydrochloride (145 mg), [1,4]dioxane-2,5-diol (55 mg), and Na(OAc)3BH (95 mg) in DCM (2 mL). LC/MS: m/z 528.6.

Sources & evidence

ORD record
ord-68425a29f92340c9a9981e21f8b4f72d
Source dataset
uspto-grants-2014_06
Patent number
US08759535B2

Reaction notes

Loading…