Isopropyl isocyanate → HCID 66679251, compound

HRID 1626713Notes

Reaction equation

HRID 1626713 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)=[C:10]([F:31])[CH:9]=2)=[O:6])[CH2:3][CH2:2]1.[CH:32]([N:35]=[C:36]=[O:37])([CH3:34])[CH3:33]>CN(C=O)C>[CH:1]1([NH:4][C:5](=[O:6])[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][N:21]([C:36]([NH:35][CH:32]([CH3:34])[CH3:33])=[O:37])[CH2:20][C:18]=4[N:19]=3)=[C:10]([F:31])[CH:9]=2)[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 61277Isopropyl isocyanateHCID 66679238HCID 66679238, compound

Product 1

HCID 66679251HCID 66679251, compoundYield 52.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

To a stirred solution of (S)-1-cyclopropyl-3-(3-fluoro-4-(4-(3-methylmorpholino)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)urea (Example 163) (100 mg, 0.23 mmol) in DMF (2 ml) was added isopropyl isocyanate (35 μl, 0.35 mmol). Reaction mixture was stirred at 20° C. for 2 hours. The crude reaction mixture was then partitioned between water (10 ml) and DCM (10 ml). The organic layer was recovered, passed through a hydrophobic frit and the solvent removed in vacuo. Residue was then purified by prep. HPLC at high pH to afford the title compound as a white solid (61 mg, 0.12 mmol, 52%)

Workup

  1. customReaction mixture
  2. customThe crude reaction mixture
  3. customwas then partitioned between water (10 ml) and DCM (10 ml)
  4. customThe organic layer was recovered
  5. customthe solvent removed in vacuo
  6. customResidue was then purified by prep

Sources & evidence

ORD record
ord-4c3afc89250442fbb7d896ab5bbec026
Source dataset
uspto-grants-2014_07
Patent number
US08785457B2

Reaction notes

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