Ethyl isocyanate → (S)-2-(4-(3-cyclopropylureido)phenyl)-N-ethyl-4-(3-methylmorpholino)-5,6-dihydropyrido[3,4-d]pyrimidine-7(8H)-carboxamide

HRID 1626602Notes

Reaction equation

HRID 1626602 reaction equation
[CH:1]1([NH:4][C:5]([NH:7][C:8]2[CH:13]=[CH:12][C:11]([C:14]3[N:15]=[C:16]([N:24]4[CH2:29][CH2:28][O:27][CH2:26][C@@H:25]4[CH3:30])[C:17]4[CH2:23][CH2:22][NH:21][CH2:20][C:18]=4[N:19]=3)=[CH:10][CH:9]=2)=[O:6])[CH2:3][CH2:2]1.[CH2:31]([N:33]=[C:34]=[O:35])[CH3:32]>C(Cl)Cl>[CH:1]1([NH:4][C:5](=[O:6])[NH:7][C:8]2[CH:9]=[CH:10][C:11]([C:14]3[N:15]=[C:16]([N:24]4[CH2:29][CH2:28][O:27][CH2:26][C@@H:25]4[CH3:30])[C:17]4[CH2:23][CH2:22][N:21]([C:34]([NH:33][CH2:31][CH3:32])=[O:35])[CH2:20][C:18]=4[N:19]=3)=[CH:12][CH:13]=2)[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 8022Ethyl isocyanateHCID 46913571(S)-1-cyclopropyl-3-(4-(4-(3-methylmorpholino)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)urea

Product 1

HCID 46913170(S)-2-(4-(3-cyclopropylureido)phenyl)-N-ethyl-4-(3-methylmorpholino)-5,6-dihydropyrido[3,4-d]pyrimidine-7(8H)-carboxamideYield 33.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-1-cyclopropyl-3-(4-(4-(3-methylmorpholino)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)urea (example 15) (102 mg, 0.25 mmol) in DCM (3 mL) at room temperature (20° C.) was added ethyl isocyanate (32 uL, 0.27 mmol). The reaction mixture was stirred for 5 h. The solvent was removed in vacuo and the residue purified by prep HPLC (low pH) to afford an orange solid (40 mg, 33%).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue purified by prep HPLC (low pH)

Sources & evidence

ORD record
ord-866a8dc55fb34009976d98b782c40887
Source dataset
uspto-grants-2014_07
Patent number
US08785457B2

Reaction notes

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