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Sodium Methoxide → HCID 178453509, compound

HRID 717740
Notes
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Reaction equation

HRID 717740 reaction equation
C[O:2][C:3](=O)[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.[Br:35][C:36]1[CH:41]=[CH:40][C:39]([C:42]2[NH:46][C:45]([NH2:47])=[N:44][CH:43]=2)=[CH:38][CH:37]=1.C[O-].[Na+]>C(O)C>[C:30]([O:29][C:27](=[O:28])[N:15]([CH2:14][C:11]1[CH:12]=[CH:13][C:8]([C:4]2[C:3](=[O:2])[N:47]=[C:45]3[NH:46][C:42]([C:39]4[CH:38]=[CH:37][C:36]([Br:35])=[CH:41][CH:40]=4)=[CH:43][N:44]3[CH:5]=2)=[CH:9][CH:10]=1)[CH2:16][CH2:17][CH2:18][NH:19][C:20]([O:22][C:23]([CH3:25])([CH3:26])[CH3:24])=[O:21])([CH3:32])([CH3:31])[CH3:33]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 10942334Sodium Methoxide2×HCID 130122555-(4-bromophenyl)-1H-imidazol-2-amineHCID 665788052-(4-{[tert-Butoxycarbonyl-(3-tert-butoxycarbonylamino-propyl)-amino]-methyl}-phenyl)-3-methoxy-acrylic acid methyl ester

Product 1

HCID 178453509HCID 178453509, compoundYield 52.1%

Reagents, catalysts & solvents 1

HCID 702
Ethanol
Solvent

Procedure

To a mixture of 2-(4-{[tert-Butoxycarbonyl-(3-tert-butoxycarbonylamino-propyl)-amino]-methyl}-phenyl)-3-methoxy-acrylic acid methyl ester (5.70 g, 11.92 mmol), 5-(4-bromo-phenyl)-1H-imidazol-2-ylamine (2.84 g, 11.92 mmol) and ethanol (60 mL) was added a solution of sodium methoxide (12 mL, 0.5 M in methanol, 6 mmol). The resulted mixture was refluxed for 18 h, additional 12 mL of sodium methoxide (0.5 M in methanol, 6 mmol) was added and continued to reflex for 20 h. The reaction was concentrated and diluted with EtOAc (300 mL) and washed with water (200 mL), brine (200 mL). The EtOAc solution was concentrated. The crude product was purified by flash chromatography (0%-8% Methanol in dichloromethane) to give desired product (4.05 g, 52%) as brown solid. 1NMR (300 MHz, CDCl3): δ 7.96 (s, 1H), 7.68 (d, J=8.1 Hz, 2H), 7.54 (m, 2H), 7.35(s, 1H), 7.27 (d, J=8.1 Hz, 2H), 5.25 (br.s, 0.5H), 4.70 (br.s, 0.5H), 4.44 (s, 2H), 3.29 (m, 2H), 3.11 (m, 2H), 1.67 (m, 2H), 1.52 (br.d, 9H), 1.44 (s, 9H). LCMS (EI) m/z: 654 (M+H+).

Workup

  1. temperatureThe resulted mixture was refluxed for 18 h
  2. concentrationThe reaction was concentrated
  3. additiondiluted with EtOAc (300 mL)
  4. washwashed with water (200 mL), brine (200 mL)
  5. concentrationThe EtOAc solution was concentrated
  6. customThe crude product was purified by flash chromatography (0%-8% Methanol in dichloromethane)

Sources & evidence

ORD record
ord-c658ce91915146a5b9844e4e7bcf37e8
Source dataset
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09193731B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes