1,3-Dioxolane → HCID 66970476, compound

HRID 1363220Notes

Reaction equation

HRID 1363220 reaction equation
[O:1]1[CH2:5][CH2:4]OC1.FC1C=CC(NC(=O)OC(C)(C)C)=C(NC2N=C(N[C@H:29]3[C:38]4C(=CC=C[CH:37]=4)[C:32](=[O:39])[CH2:31][CH2:30]3)C([N+]([O-])=O)=CN=2)C=1.FC1C=CC(NC(=O)OC(C)(C)C)=C(NC2N=C(SC#N)C([N+]([O-])=O)=CN=2)C=1.[NH2:71][C@H:72]1[C:81]2[C:76](=[CH:77][CH:78]=[CH:79][CH:80]=2)[C:75](=[O:82])[CH2:74][CH2:73]1>CN(C=O)C.CCOC(C)=O>[O:82]=[C:75]1[C:76]2[C:81](=[CH:80][CH:79]=[CH:78][CH:77]=2)[C@H:72]([N:71]2[C:5](=[O:1])[C:4]3[C:31](=[CH:30][CH:29]=[CH:38][CH:37]=3)[C:32]2=[O:39])[CH2:73][CH2:74]1

Participants

7

Reactant 4

HCID 125861,3-Dioxolane2×HCID 59704889tert-Butyl 4-fluoro-2-(5-nitro-4-thiocyanatopyrimidin-2-ylamino)phenylcarbamateHCID 66926982HCID 66926982, compoundHCID 66970493HCID 66970493, compound

Product 1

HCID 66970476HCID 66970476, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

1,3-Dioxolane of (R)-tert-butyl 4-fluoro-2-(5-nitro-4-(4-oxo-1,2,3,4-tetrahydronaphthalen-1-ylamino)pyrimidin-2-ylamino)phenylcarbamate. A solution of tert-butyl 4 fluoro-2-(5-nitro-4-thiocyanatopyrimidin-2-ylamino)phenylcarbamate (170 mg), 1,3-Dioxolane of (R)-4-amino-3,4-dihydronaphthalen-1(2H)-one (85 mg), and TEA (0.2 mL) in DMF (5 mL) was stirred at room temperature overnight. The reaction mixture was diluted with EtOAc, washed with saturated brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by PTLC (EtOAc/hexane, 50/50) to afford 150 mg of the title compound.

Workup

  1. washwashed with saturated brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by PTLC (EtOAc/hexane, 50/50)

Sources & evidence

ORD record
ord-96314ac450ab4985985ebbdfc7558b18
Source dataset
uspto-grants-2011_02
Patent number
US07884109B2

Reaction notes

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