Allyl bromide → HCID 86656629, compound

HRID 882890Notes

Reaction equation

HRID 882890 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH3:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][CH2:18][N:19]([CH2:34][CH2:35][CH2:36][C:37]2[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[CH:39][CH:38]=2)[CH2:20][CH2:21][NH:22][C:23]([C:25]2[C:30]([NH2:31])=[N:29][C:28]([NH2:32])=[C:27]([Cl:33])[N:26]=2)=[O:24])=[CH:12][CH:11]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH2:51](Br)[CH:52]=[CH2:53]>CC(C)=O>[F:1][C:2]([F:7])([F:6])[C:3]([O-:5])=[O:4].[CH2:53]([N+:19]([CH2:20][CH2:21][NH:22][C:23]([C:25]1[C:30]([NH2:31])=[N:29][C:28]([NH2:32])=[C:27]([Cl:33])[N:26]=1)=[O:24])([CH2:34][CH2:35][CH2:36][C:37]1[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[CH:39][CH:38]=1)[CH2:18][CH2:17][CH2:16][C:13]1[CH:14]=[CH:15][C:10]([O:9][CH3:8])=[CH:11][CH:12]=1)[CH:52]=[CH2:51]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 10340Sodium CarbonateHCID 86656630HCID 86656630, compound2×

Product 1

HCID 86656629HCID 86656629, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 3,5-diamino-6-chloro-pyrazine-2-carboxylic acid (2-{bis-[3-(4-methoxy-phenyl)-propyl]-amino}-ethyl)-amide trifluoroacetate (Intermediate D) (0.20 g, 0.31 mmol) in acetone (5 mL) is added sodium carbonate (99 mg, 0.94 mmol) followed by allyl bromide (0.082 mL, 0.94 mmol). The reaction mixture is heated at reflux for 72 h, cooled to RT then filtered to remove inorganic salts. The filtrate is concentrated and purification by reverse phase column chromatography (Isolute™ C18, 0-100% acetonitrile in water with 0.1% TFA) affords the title compound. M+ 567. 1H NMR (400 MHz, DMSO-d6) δ 8.32 (1H, t), 7.76 (2H, br), 7.16 (2H, br), 7.11 (4H, d), 6.85 (4H, d), 5.95 (1H, ddt) 5.62 (1H, d), 5.57 (1H, d), 3.99 (2H, d), 3.72 (6H, s), 3.58-3.54 (2H, m), 3.30 (2H, t), 3.24-3.20 (4H, m), 2.50 (4H, t), 1.97-1.78 (4H, m).

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for 72 h
  3. filtrationthen filtered
  4. customto remove inorganic salts
  5. concentrationThe filtrate is concentrated
  6. custompurification by reverse phase column chromatography (Isolute™ C18, 0-100% acetonitrile in water with 0.1% TFA)

Sources & evidence

ORD record
ord-0c68d7c2e67f4c70848d456c258344b8
Source dataset
uspto-grants-2012_08
Patent number
US08236808B2

Reaction notes

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