Bis(2-amino-1H-imidazole) sulphate → HCID 178453510, compound

HRID 717738Notes

Reaction equation

HRID 717738 reaction equation
CO[C:3](=[O:34])[C:4]([C:8]1[CH:13]=[CH:12][C:11]([CH2:14][N:15]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:16][CH2:17][CH2:18][NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[CH:10][CH:9]=1)=[CH:5]OC.S(O)(O)(=O)=O.[NH:40]1[CH:44]=[CH:43][N:42]=[C:41]1[NH2:45].C[O-].[Na+]>C(O)C>[C:23]([O:22][C:20](=[O:21])[NH:19][CH2:18][CH2:17][CH2:16][N:15]([C:27]([O:29][C:30]([CH3:31])([CH3:32])[CH3:33])=[O:28])[CH2:14][C:11]1[CH:12]=[CH:13][C:8]([C:4]2[C:3](=[O:34])[N:45]=[C:41]3[NH:42][CH:43]=[CH:44][N:40]3[CH:5]=2)=[CH:9][CH:10]=1)([CH3:24])([CH3:26])[CH3:25]

Participants

5

Reactant 3

HCID 135136Bis(2-amino-1H-imidazole) sulphateHCID 10942334Sodium Methoxide2×HCID 665788052-(4-{[tert-Butoxycarbonyl-(3-tert-butoxycarbonylamino-propyl)-amino]-methyl}-phenyl)-3-methoxy-acrylic acid methyl ester

Product 1

HCID 178453510HCID 178453510, compoundYield 48.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 2-(4-{[tert-Butoxycarbonyl-(3-tert-butoxycarbonylamino-propyl)-amino]-methyl}-phenyl)-3-methoxy-acrylic acid methyl ester (97 mg, 0.2 mmol), 1H-imidazol-2-ylamine sulfate (29 mg, 0.223 mmol) and ethanol (10 mL) was added a solution of sodium methoxide (0.5 mL, 0.5 M in methanol, 0.25 mmol). The resulted mixture was refluxed for 18 h, additional 0.5 mL of sodium methoxide (0.5 M in methanol, 0.5 mmol) was added and continued to reflex for 20 h. The reaction was concentrated and diluted with EtOAc (30 mL) and washed with water (20 mL), brine (20 mL). The EtOAc solution was concentrated. The crude product was purified by flash chromatography (10% methanol in dichloromethane) to give desired product (48 mg, 48%) as white solid. 1NMR (300 MHz, CD3OD): δ 8.40 (s, 1H), 7.59 (br.s, 2H), 7.29 (m, 4H), 4.46 (s, 2H), 3.23 (m, 2H), 3.02 (m, 2H), 1.68 (m, 2H), 1.52 (br.d, 9H), 1. 42 (s, 9H). LCMS (EI) m/z: 498.1 (M+H+).

Workup

  1. temperatureThe resulted mixture was refluxed for 18 h
  2. concentrationThe reaction was concentrated
  3. additiondiluted with EtOAc (30 mL)
  4. washwashed with water (20 mL), brine (20 mL)
  5. concentrationThe EtOAc solution was concentrated
  6. customThe crude product was purified by flash chromatography (10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-7994259b567445fa94a6c609771e7e26
Source dataset
uspto-grants-2015_11
Patent number
US09193731B2

Reaction notes

Loading…