Cyclopropanecarbonyl chloride → HCID 46912705, compound

HRID 1626571Notes

Reaction equation

HRID 1626571 reaction equation
FC(F)(F)C(O)=O.[CH:8]1([NH:11][C:12]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[N:22]=[C:23]([N:31]4[CH2:36][CH2:35][O:34][CH2:33][C@@H:32]4[CH3:37])[C:24]4[CH2:30][CH2:29][NH:28][CH2:27][C:25]=4[N:26]=3)=[CH:17][CH:16]=2)=[O:13])[CH2:10][CH2:9]1.CCN(C(C)C)C(C)C.[CH:47]1([C:50](Cl)=[O:51])[CH2:49][CH2:48]1>C(Cl)Cl>[CH:47]1([C:50]([N:28]2[CH2:29][CH2:30][C:24]3[C:23]([N:31]4[CH2:36][CH2:35][O:34][CH2:33][C@@H:32]4[CH3:37])=[N:22][C:21]([C:18]4[CH:17]=[CH:16][C:15]([NH:14][C:12]([NH:11][CH:8]5[CH2:9][CH2:10]5)=[O:13])=[CH:20][CH:19]=4)=[N:26][C:25]=3[CH2:27]2)=[O:51])[CH2:49][CH2:48]1

Participants

5

Reactant 3

HCID 77637Cyclopropanecarbonyl chlorideHCID 81531DiisopropylethylamineHCID 66687855HCID 66687855, compound

Product 1

HCID 46912705HCID 46912705, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (S)-1-cyclopropyl-3-(4-(4-(3-methylmorpholino)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)urea 2,2,2-trifluoroacetate (106 mg, 0.26 mmol) in DCM was added iPr2NEt (91 uL, 0.52 mmol) and cyclopropane carbonyl chloride (26 uL, 0.29 mmol). The reaction mixture was stirred at room temperature for 16 h. The reaction mixture was concentrated and triturated from Et2O:MeOH (10:1) to give a white solid (69 mg, 0.15 mmol, 58% yield).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customtriturated from Et2O:MeOH (10:1)

Sources & evidence

ORD record
ord-5e4d4c5457214aa6acc7e1393675e5ca
Source dataset
uspto-grants-2014_07
Patent number
US08785457B2

Reaction notes

Loading…