Isopropanol → Methyl 3-(2,3-dihydroxypropyl)amino-2-[3-chloro-6-(methylcarbonyl)amino-5-nitropyrazin-2-yl]-2-butenoate

HRID 1903070Notes

Reaction equation

HRID 1903070 reaction equation
C(O)(C)C.[Cl:5][C:6]1[N:7]=[C:8]([N+:17]([O-:19])=[O:18])[C:9]([NH:13][C:14](=[O:16])[CH3:15])=[N:10][C:11]=1Cl.[OH:20][CH:21]([CH2:31][OH:32])[CH2:22][NH:23][C:24]([CH3:30])=[CH:25][C:26]([O:28][CH3:29])=[O:27]>C(N(CC)CC)C>[OH:20][CH:21]([CH2:31][OH:32])[CH2:22][NH:23][C:24]([CH3:30])=[C:25]([C:11]1[C:6]([Cl:5])=[N:7][C:8]([N+:17]([O-:19])=[O:18])=[C:9]([NH:13][C:14]([CH3:15])=[O:16])[N:10]=1)[C:26]([O:28][CH3:29])=[O:27]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 13062977N-(5,6-Dichloro-3-nitropyrazin-2-yl)acetamideHCID 71430100Methyl 3-[(2,3-dihydroxypropyl)amino]but-2-enoate

Product 1

HCID 86739301Methyl 3-(2,3-dihydroxypropyl)amino-2-[3-chloro-6-(methylcarbonyl)amino-5-nitropyrazin-2-yl]-2-butenoate

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To 50 ml isopropanol is added 2.0 g (0.008 m) N-(5,6-dichloro-3-nitropyrazinyl)acetamide (8), 1.32 g (0.007 m) methyl 3-(2,3-dihydroxypropyl) amino-2-butenoate (3), and 0.81 g (0.008 m) triethylamine. This dark solution is stirred at room temperature for five days. The solvents are then removed on the rotary evaporator and the residue is chromatographed on silica gel and is eluted with 8% methanol/chloroform. Material with Rf =0.5 is collected. This material is a reddish brown solid and is further purified by high pressure liquid chromatography to afford 9 as a brown solid, m.p. 70°-73°.

Workup

  1. customThe solvents are then removed on the rotary evaporator
  2. customthe residue is chromatographed on silica gel
  3. washis eluted with 8% methanol/chloroform
  4. customMaterial with Rf =0.5 is collected
  5. customis further purified by high pressure liquid chromatography

Sources & evidence

ORD record
ord-2ac811d7e0bd4aa59a2dba86d4e12bfa
Source dataset
uspto-grants-1984_03
Patent number
US04435400

Reaction notes

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