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Hydrochloric Acid → [3-Amino-6-(3,4-dichloro-phenyl)-pyrazin-2-yl]-(4-piperidin-1-ylmethyl-phenyl)-methanone

HRID 2387191
Notes
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Reaction equation

HRID 2387191 reaction equation
[N:1]1([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([Mg]Br)=[CH:10][CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CON(C)[C:19]([C:21]1[C:26]([NH2:27])=[N:25][CH:24]=[C:23]([C:28]2[CH:33]=[CH:32][C:31]([Cl:34])=[C:30]([Cl:35])[CH:29]=2)[N:22]=1)=[O:20].Cl>C1COCC1>[NH2:27][C:26]1[C:21]([C:19]([C:11]2[CH:12]=[CH:13][C:8]([CH2:7][N:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)=[CH:9][CH:10]=2)=[O:20])=[N:22][C:23]([C:28]2[CH:33]=[CH:32][C:31]([Cl:34])=[C:30]([Cl:35])[CH:29]=2)=[CH:24][N:25]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 866345423-Amino-6-(3,4-dichloro-phenyl)-pyrazine-2-carboxylic acid methoxy-methyl amide2×HCID 178419630HCID 178419630, compound

Product 1

HCID 44233342[3-Amino-6-(3,4-dichloro-phenyl)-pyrazin-2-yl]-(4-piperidin-1-ylmethyl-phenyl)-methanone

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent
2×

Conditions

Temperature
0 °C

Procedure

A solution of 0.25 M [4-(1-piperidinyl-methyl)phenyl]magnesium bromide in THF (5.51 ml, 1.37 mmol) is added dropwise to a solution of 3-amino-6-(3,4-dichloro-phenyl)-pyrazine-2-carboxylic acid methoxy-methyl amide (Intermediate B) (0.09 g, 0.27 mmol) in THF (5 ml) and the resulting solution is stirred for 2 hours. The solution is cooled to 0° C., and 2M HCl (10 ml) is added. The solution is washed with EtOAc (20 ml) and then the pH is adjusted to 11 using 2M NaOH. Extraction with EtOAc (50 ml), drying (MgSO4) and removal of solvent in vacuo affords a yellow oil. Purification by flash chromatography (SiO2, 50-100% EtOAc in iso-hexane) followed by trituration with methanol affords the title compound as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 9.04 (1H, s), 8.12 (1H, d), 7.97 (2H, bs), 7.93-7.88 (3H, m), 7.71 (1H, d), 7.47 (2H, d), 3.54 (2H, s), 2.36 (4H, bs), 1.52-1.51 (4H, m), 1.43-1.37 (2H, m); MS m/z 441, 443 [M+H]+

Workup

  1. washThe solution is washed with EtOAc (20 ml)
  2. extractionExtraction with EtOAc (50 ml)
  3. customdrying
  4. custom(MgSO4) and removal of solvent in vacuo
  5. customaffords a yellow oil
  6. customPurification by flash chromatography (SiO2, 50-100% EtOAc in iso-hexane)

Sources & evidence

ORD record
ord-606be6eeab93436a9f1b6b53635c819a
Source dataset
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08268834B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes