Diisopropylethylamine → 1-{2-[(4-Hydroxypiperidine-1-carbonyl)-amino]-ethyl}-1H-benzoimidazole-5-carboxylic Acid (5-hydroxy-adamantan-2-yl)-amide

HRID 555301Notes

Reaction equation

HRID 555301 reaction equation
[OH:1][C:2]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:4]([CH:5]3[NH:12][C:13]([C:15]3[CH:26]=[CH:25][C:18]4[N:19]([CH2:22][CH2:23][NH2:24])[CH:20]=[N:21][C:17]=4[CH:16]=3)=[O:14])[CH2:3]1)[CH2:9]2.CCN(C(C)C)C(C)C.[OH:36][CH:37]1[CH2:42][CH2:41][N:40]([C:43](Cl)=[O:44])[CH2:39][CH2:38]1>C1COCC1>[OH:1][C:2]12[CH2:3][CH:4]3[CH2:10][CH:8]([CH2:7][CH:6]([CH:5]3[NH:12][C:13]([C:15]3[CH:26]=[CH:25][C:18]4[N:19]([CH2:22][CH2:23][NH:24][C:43]([N:40]5[CH2:41][CH2:42][CH:37]([OH:36])[CH2:38][CH2:39]5)=[O:44])[CH:20]=[N:21][C:17]=4[CH:16]=3)=[O:14])[CH2:11]1)[CH2:9]2

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 669876871-(2-aminoethyl)-1H-benzimidazole-5-carboxylic acid (5-hydroxy-adamantan-2-yl)-amideHCID 866300624-Hydroxypiperidine-1-carbonyl Chloride

Product 1

HCID 576851361-{2-[(4-Hydroxypiperidine-1-carbonyl)-amino]-ethyl}-1H-benzoimidazole-5-carboxylic Acid (5-hydroxy-adamantan-2-yl)-amide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(2-aminoethyl)-1H-benzimidazole-5-carboxylic acid (5-hydroxy-adamantan-2-yl)-amide (0.35 g, 0.988 mmol) in dry THF (5 mL) was added DIPEA (0.3 mL, 1.91 mmol) at 0° C. To this reaction mixture was added 4-hydroxypiperidine-1-carbonyl chloride slowly and stirred for 2 h at ambient temperature. The solvents were evaporated and the residue purified by preparative HPLC cis and trans isomers of 1-{2-[(4-hydroxypiperidine-1-carbonyl)-amino]-ethyl}-1H-benzimidazole-5-carboxylic acid (5-hydroxyadamantan-2-yl)amide.

Workup

  1. customThe solvents were evaporated
  2. customthe residue purified by preparative HPLC cis and trans isomers of 1-{2-[(4-hydroxypiperidine-1-carbonyl)-amino]-ethyl}-1H-benzimidazole-5-carboxylic acid (5-hydroxyadamantan-2-yl)amide

Sources & evidence

ORD record
ord-81b2c7e68e5d4efcad649b5fbb15a4b1
Source dataset
uspto-grants-2011_11
Patent number
US08053431B2

Reaction notes

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