Cyclopropanecarbonyl chloride → (S)-1-(4-(7-(cyclopropanecarbonyl)-4-(3-methylmorpholino)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)-3-ethylurea

HRID 1626570Notes

Reaction equation

HRID 1626570 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([NH:10][C:11]([NH:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[N:21]=[C:22]([N:30]3[CH2:35][CH2:34][O:33][CH2:32][C@@H:31]3[CH3:36])[C:23]3[CH2:29][CH2:28][NH:27][CH2:26][C:24]=3[N:25]=2)=[CH:16][CH:15]=1)=[O:12])[CH3:9].CCN(C(C)C)C(C)C.[CH:46]1([C:49](Cl)=[O:50])[CH2:48][CH2:47]1>C(Cl)Cl>[CH:46]1([C:49]([N:27]2[CH2:28][CH2:29][C:23]3[C:22]([N:30]4[CH2:35][CH2:34][O:33][CH2:32][C@@H:31]4[CH3:36])=[N:21][C:20]([C:17]4[CH:16]=[CH:15][C:14]([NH:13][C:11]([NH:10][CH2:8][CH3:9])=[O:12])=[CH:19][CH:18]=4)=[N:25][C:24]=3[CH2:26]2)=[O:50])[CH2:48][CH2:47]1

Participants

5

Reactant 3

HCID 77637Cyclopropanecarbonyl chlorideHCID 81531DiisopropylethylamineHCID 66687590HCID 66687590, compound

Product 1

HCID 46912701(S)-1-(4-(7-(cyclopropanecarbonyl)-4-(3-methylmorpholino)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)-3-ethylureaYield 15%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (S)-1-ethyl-3-(4-(4-(3-methylmorpholino)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)urea 2,2,2-trifluoroacetate (100 mg, 0.20 mmol) in DCM was added iPr2NEt (70 uL, 0.40 mmol) and cyclopropanecarbonyl chloride (20 uL, 0.22 mmol). The reaction mixture was stirred at room temperature for 16 h. The reaction mixture was concentrated and purified by prep. HPLC to give a white solid (14 mg, 0.03 mmol, 15% yield).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by prep

Sources & evidence

ORD record
ord-8328e913cc8b4dacad1ae7f24d4e9e2f
Source dataset
uspto-grants-2014_07
Patent number
US08785457B2

Reaction notes

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