Cyclobutanecarbonyl chloride → HCID 46843818, compound

HRID 533774Notes

Reaction equation

HRID 533774 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]2[O:6][CH2:7][O:8][C:4]=2[C:3]=1[NH:11][C:12]1[C:20]2[C:19]3[CH2:21][NH:22][CH2:23][CH2:24][C:18]=3[NH:17][C:16]=2[N:15]=[CH:14][CH:13]=1.CCN(C(C)C)C(C)C.[CH:34]1([C:38](Cl)=[O:39])[CH2:37][CH2:36][CH2:35]1>ClCCCl>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]2[O:6][CH2:7][O:8][C:4]=2[C:3]=1[NH:11][C:12]1[C:20]2[C:19]3[CH2:21][N:22]([C:38]([CH:34]4[CH2:37][CH2:36][CH2:35]4)=[O:39])[CH2:23][CH2:24][C:18]=3[NH:17][C:16]=2[N:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 78705Cyclobutanecarbonyl chlorideHCID 81531DiisopropylethylamineHCID 66677984HCID 66677984, compound

Product 1

HCID 46843818HCID 46843818, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

(5-Chloro-benzo[1,3]dioxol-4-yl)-(6,7,8,9-tetrahydro-5H-dipyrido[2,3-b;3′,4′-d]pyrrol-4-yl)-amine (100 mg, 0.29 mmol) and DIEA (0.15 mL, 0.88 mmol) were dissolved in 1,2-dichloroethane (2 mL) and stirred at room temperature. Cyclobutanecarbonyl chloride (0.04 mL, 0.35 mmol) was added dropwise, and the reaction was stirred for 1 h at room temperature. The reaction was concentrated. The crude material was dissolved in DMSO (3 mL) and filtered. The filtrate was purified directly via prep-LC-MS to provide 69 (37 mg, 30% yield) as a white fluffy solid. LC-MS (M+H=425, obsd.=425).

Workup

  1. stirringthe reaction was stirred for 1 h at room temperature
  2. concentrationThe reaction was concentrated
  3. dissolutionThe crude material was dissolved in DMSO (3 mL)
  4. filtrationfiltered
  5. customThe filtrate was purified directly via prep-LC-MS

Sources & evidence

ORD record
ord-66a9e4fe303f4f3588b9a034e5f290cd
Source dataset
uspto-grants-2014_10
Patent number
US08853391B2

Reaction notes

Loading…