4-Chlorobenzoyl chloride → HCID 58243412, compound

HRID 2361687Notes

Reaction equation

HRID 2361687 reaction equation
[CH:1]1([N:5]2[CH2:11][CH2:10][CH2:9][N:8]([C:12]([N:14]3[CH2:17][CH:16]([NH2:18])[CH2:15]3)=[O:13])[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1.[Cl:19][C:20]1[CH:28]=[CH:27][C:23]([C:24](Cl)=[O:25])=[CH:22][CH:21]=1.CCN(C(C)C)C(C)C>ClC(Cl)C.ClCCl>[Cl:19][C:20]1[CH:28]=[CH:27][C:23]([C:24]([NH:18][CH:16]2[CH2:15][N:14]([C:12]([N:8]3[CH2:9][CH2:10][CH2:11][N:5]([CH:1]4[CH2:4][CH2:3][CH2:2]4)[CH2:6][CH2:7]3)=[O:13])[CH2:17]2)=[O:25])=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 85014-Chlorobenzoyl chlorideHCID 81531DiisopropylethylamineHCID 44477248HCID 44477248, compound

Product 1

HCID 58243412HCID 58243412, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of 1-[(4-cyclobutyl-1,4-diazepan-1-yl)carbonyl]azetidin-3-amine (46 mg, 0.18 mmol) in dichloroethane (3 ml) was added 4-chlorobenzoyl chloride (20 μl, 0.18 mmol) and DIPEA (38 μl, 0.22 mmol). The reaction was stirred at room temperature for 3 hours and then diluted with dichloromethane (30 ml) and washed twice with saturated NaHCO3 (15 ml), dried (MgSO4), filtered and concentrated at reduced pressure. The residue was purified by FCC (DCM/MeOH/NH3 with gradient, 98:2:1 to 90:10:1) to provide the title compound as white solid (26 mg, 37%).

Workup

  1. washwashed twice with saturated NaHCO3 (15 ml)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated at reduced pressure
  5. customThe residue was purified by FCC (DCM/MeOH/NH3 with gradient, 98:2:1 to 90:10:1)

Sources & evidence

ORD record
ord-fd537f77684249b28f866668e847fc8e
Source dataset
uspto-grants-2014_04
Patent number
US08691804B2

Reaction notes

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