Hydrochloric Acid → 4-({4-[(4-tert-Butoxycarbonylamino-1-methyl-1H-pyrrole-2-carbonyl)-amino]-1-methyl-1H-imidazole-2-carbonyl}-amino)-1-methyl-1H-imidazole-2-carboxylic acid ethyl ester

HRID 476405

Reaction equation

HRID 476405 reaction equation
C(C1NC=CN=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=O.[CH2:13]([O:15][C:16]([C:18]1[N:19]([CH3:40])[CH:20]=[C:21]([NH:23][C:24]([C:26]2[N:27]([CH3:39])[CH:28]=[C:29]([NH:31][C:32]([O:34]C(C)(C)C)=O)[N:30]=2)=[O:25])[N:22]=1)=[O:17])[CH3:14].Cl.N1C=CC=C1.CCN=[C:50]=[N:51][CH2:52][CH2:53][CH2:54][N:55]([CH3:57])[CH3:56].[O:58]1CCOCC1>CN(C=O)C.CN(C1C=CN=CC=1)C>[CH2:13]([O:15][C:16]([C:18]1[N:19]([CH3:40])[CH:20]=[C:21]([NH:23][C:24]([C:26]2[N:27]([CH3:39])[CH:28]=[C:29]([NH:31][C:32]([C:54]3[N:55]([CH3:56])[CH:57]=[C:52]([NH:51][C:50]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:58])[CH:53]=3)=[O:34])[N:30]=2)=[O:25])[N:22]=1)=[O:17])[CH3:14]

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 8027PyrroleHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 312751,4-DioxaneHCID 22359409Tert-butyloxycarbonylimidazoleHCID 597990864-[(4-tert-Butoxycarbonylamino-1-methyl-1H-imidazole-2-carbonyl)-amino]-1-methyl-1H-imidazole-2-carboxylic acid ethyl ester

Product 1

HCID 688766714-({4-[(4-tert-Butoxycarbonylamino-1-methyl-1H-pyrrole-2-carbonyl)-amino]-1-methyl-1H-imidazole-2-carbonyl}-amino)-1-methyl-1H-imidazole-2-carboxylic acid ethyl esterYield 32%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

The Boc imidazole dimer (39) (0.253 g, 0.65 mmol) was deprotected using 4M HCl in dioxane as described in general procedure C. The resulting residue (39′) was dissolved in dry DMF (5 mL) and the Boc protected pyrrole acid (2) (0.156 g, 0.65 mmol) was added. The resulting solution was treated with EDCI (1.5 equiv.) and DMAP (2 equiv.) and reacted as described in general procedure A. This yielded a brown foam 0.109 g (32%). LCMS (method 2) rt=1.87 min; m/z (ES+) 515 (M+1).

Workup

  1. additionwas added
  2. customreacted

Sources & evidence

ORD record
ord-864bdf0671364083a41efb50b0de7fee
Source dataset
uspto-grants-2014_01
Patent number
US08637664B2

Linked notes

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