4-Chlorobenzoyl chloride → HCID 46843218, compound

HRID 533735Notes

Reaction equation

HRID 533735 reaction equation
[Cl:1][C:2]1[CH:14]=[N:13][C:5]2[NH:6][C:7]3[CH2:12][CH2:11][NH:10][CH2:9][C:8]=3[C:4]=2[CH:3]=1.CCN(C(C)C)C(C)C.[Cl:24][C:25]1[CH:33]=[CH:32][C:28]([C:29](Cl)=[O:30])=[CH:27][CH:26]=1>C1COCC1>[ClH:1].[Cl:24][C:25]1[CH:33]=[CH:32][C:28]([C:29]([N:10]2[CH2:11][CH2:12][C:7]3[NH:6][C:5]4[N:13]=[CH:14][C:2]([Cl:1])=[CH:3][C:4]=4[C:8]=3[CH2:9]2)=[O:30])=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 85014-Chlorobenzoyl chlorideHCID 81531DiisopropylethylamineHCID 66677239HCID 66677239, compound

Product 1

HCID 46843218HCID 46843218, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Chloro-6,7,8,9-tetrahydro-5H-dipyrido[2,3-b;3′,4′-d]pyrrole (50 mg, 0.24 mmol) and DIEA (0.05 L, 0.29 mmol) were dissolved in THF (2 ml) and stirred at room temperature. 4-Chlorobenzoyl chloride (0.04 mL, 0.29 mmol) was added dropwise, and the reaction was stirred for 1 h at room temperature. The reaction was quenched with H2O (200 mL). The resulting precipitate was filtered, and dried overnight under vacuum. The HCl salt was formed via dissolving the precipitate in MeOH (2 ml) and adding 1 M HCl/ether (2 equivalents), and cooling at 0° C. overnight. The resulting precipitate was filtered, and dried under vacuum to provide 18 (54 mg, 59% yield) as a yellow powder. LC-MS (M+H=346, obsd.=346).

Workup

  1. stirringthe reaction was stirred for 1 h at room temperature
  2. customThe reaction was quenched with H2O (200 mL)
  3. filtrationThe resulting precipitate was filtered
  4. customdried overnight under vacuum

Sources & evidence

ORD record
ord-bf7e0fdbb4704a1da93fc5fc26bfa9ef
Source dataset
uspto-grants-2014_10
Patent number
US08853391B2

Reaction notes

Loading…