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1,2-Dichloroethane → Methyl 4-(4-(tert-butoxycarbonylamino)-1-methyl-1H-imidazole-2-carboxamido)-1-methyl-1H-imidazole-2-carboxylate

HRID 1776667
Notes
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Reaction equation

HRID 1776667 reaction equation
C(OC([NH:8][C:9]1[N:10]=[C:11]([C:15]([O:17][CH3:18])=[O:16])[N:12]([CH3:14])[CH:13]=1)=O)(C)(C)C.Cl.[C:20]([O:24][C:25]([NH:27][C:28]1[N:29]=[C:30]([C:34]([OH:36])=O)[N:31]([CH3:33])[CH:32]=1)=[O:26])([CH3:23])([CH3:22])[CH3:21].C(Cl)CCl.CCN(C(C)C)C(C)C>C(O)C.C1(C)C=CC=CC=1.CC(N(C)C)=O>[C:20]([O:24][C:25]([NH:27][C:28]1[N:29]=[C:30]([C:34]([NH:8][C:9]2[N:10]=[C:11]([C:15]([O:17][CH3:18])=[O:16])[N:12]([CH3:14])[CH:13]=2)=[O:36])[N:31]([CH3:33])[CH:32]=1)=[O:26])([CH3:21])([CH3:22])[CH3:23]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 5

HCID 111,2-DichloroethaneHCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 27572264-(((1,1-Dimethylethoxy)carbonyl)amino)-1-methyl-1H-imidazole-2-carboxylic acidHCID 11379828METHYL 4-(TERT-BUTOXYCARBONYLAMINO)-1-METHYL-1H-IMIDAZOLE-2-CARBOXYLATE

Product 1

HCID 59440227
Methyl 4-(4-(tert-butoxycarbonylamino)-1-methyl-1H-imidazole-2-carboxamido)-1-methyl-1H-imidazole-2-carboxylate
Yield 71.5%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 1140TolueneSolventHCID 31374DimethylacetamideSolvent

Procedure

Methyl 4-(tert-butoxycarbonylamino)-1-methyl-1H-imidazole-2-carboxylate (2.50 g, 9.80 mmol) in 30 ml of EtAc was added 6 ml of HCl (conc.). After stirred for 30 min, the mixture was diluted with ethanol and toluene, concentrated and co-evaporated with ethanol/toluene (1:1, 3×50 ml) to dryness compound without further purification. To the dryness compound was added 4-(tert-butoxycarbonylamino)-1-methyl-1H-imidazole-2-carboxylic acid (2.36 g, 9.8 mmol), EDC (5.90 g, 30.7 mmol), DIPEA (1.70 ml, 9.8 mmol) and 80 ml of DMA. The mixture was stirred under Ar overnight, concentrated, diluted with THF/EtAc (1:2, 150 ml), and washed 1M NaH2PO4/NaCl (conc) and NaHCO3 (conc) separately. The organic solvent layer was separated and dried over MgSO4, filtered, concentrated and purified on SiO2 chromatography eluted with EtAc/DCM (1:25 to 1:15) to afford 2.65 g (71.5%) of the title product. 1H NMR (DMSO) 11.17 (s, 1H), 10.48 (s, 1H), 7.58 (s, 1H), 7.32 (s, 1H), 4.01 (s, 3H), 3.94 (s, 3H), 3.92 (s, 3H), 1.45 (s, 9H); 13C NMR 160.60, 157.30, 135.92, 135.45, 132.86, 126.12, 114.83, 79.50, 52.70, 35.58, 34.92, 28.08; MS m/z+401.8 (M+Na).

Workup

  1. concentrationconcentrated and co-evaporated with ethanol/toluene (1:1, 3×50 ml) to dryness compound without further purification
  2. stirringThe mixture was stirred under Ar overnight
  3. concentrationconcentrated
  4. additiondiluted with THF/EtAc (1:2, 150 ml)
  5. washwashed 1M NaH2PO4/NaCl (conc) and NaHCO3 (conc) separately
  6. customThe organic solvent layer was separated
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. custompurified on SiO2 chromatography
  11. washeluted with EtAc/DCM (1:25 to 1:15)

Sources & evidence

ORD record
ord-4562bba0de8b4bdcb523c009ca79a906
Source dataset
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09265841B2

Reaction notes

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