1,1'-Carbonyldiimidazole → HCID 136038645, compound

HRID 1992411Notes

Reaction equation

HRID 1992411 reaction equation
Cl.[CH2:2]([O:9][C:10]1[CH:11]=[C:12]([CH:16]([NH2:24])[C:17]2[C:22]([Cl:23])=[N:21][CH:20]=[CH:19][N:18]=2)[CH:13]=[CH:14][CH:15]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C1N=CN([C:30](N2C=NC=C2)=[O:31])C=1.CCN(C(C)C)C(C)C>C1COCC1>[CH2:2]([O:9][C:10]1[CH:11]=[C:12]([C:16]2[NH:24][C:30](=[O:31])[N:18]3[CH:19]=[CH:20][N:21]=[C:22]([Cl:23])[C:17]=23)[CH:13]=[CH:14][CH:15]=1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 86604615C-(3-benzyloxyphenyl)-C-(3-chloropyrazin-2-yl)methylamine hydrochloride

Product 1

HCID 136038645HCID 136038645, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

A solution C-(3-benzyloxy-phenyl)-C-(3-chloro-pyrazin-2-yl)-methylamine hydrochloride (5 g, 13.8 mmol) and CDI (2.46 g, 15.19 mmol) in anhydrous THF (70 mL) was charged with DIEA (2.40 mL, 13.8 mmol) and heated to 80° C. for 1 h and then concentrated in vacuo. The crude material was partitioned between EtOAc and H2O and separated. The aqueous layer was washed with EtOAc (3×) and the combined organic layers were washed with brine (1×), dried over Na2SO4, filtered and concentrated in vacuo. The crude was purified by chromatography on silica gel [eluting with 5% MeOH in DCM], to yield the desired product as a yellow solid; 1H NMR (DMSO-d6, 400 MHz) δ 5.17 (s, 2H), 6.86 (d, J=5.2 Hz, 1H), 7.10-7.16 (m, 2H), 7.22-7.23 (m, 1H), 7.34-7.48 (m, 6H), 7.50 (d, J=7.9 Hz, 1H); MS (ES+): m/z=352.15 (100) [MH+], HPLC: tR=3.19 min (MicromassZQ, polar—5 min)

Workup

  1. concentrationconcentrated in vacuo
  2. customThe crude material was partitioned between EtOAc and H2O
  3. customseparated
  4. washThe aqueous layer was washed with EtOAc (3×)
  5. washthe combined organic layers were washed with brine (1×)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude was purified by chromatography on silica gel [eluting with 5% MeOH in DCM]

Sources & evidence

ORD record
ord-61d16fff6fbf42ddaea4b2fc2a785be8
Source dataset
uspto-grants-2010_01
Patent number
US07648987B2

Reaction notes

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