Isopropanol → HCID 57664251, compound

HRID 1919635Notes

Reaction equation

HRID 1919635 reaction equation
[CH:1]1([NH:4][C:5]2[N:6]=[CH:7][C:8]3[C:17]4[CH:16]=[CH:15][C:14](C(O)=O)=[CH:13][C:12]=4[N:11]=[C:10]([NH:21][C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=4)[C:9]=3[N:32]=2)[CH2:3][CH2:2]1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:40])C=CC=CC=1.C([N:52]([CH2:55]C)CC)C.[CH:57]([OH:60])([CH3:59])[CH3:58]>>[CH:1]1([NH:4][C:5]2[N:6]=[CH:7][C:8]3[C:17]4[CH:16]=[CH:15][C:14]([NH:52][C:55](=[O:40])[O:60][CH:57]([CH3:59])[CH3:58])=[CH:13][C:12]=4[N:11]=[C:10]([NH:21][C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:29])([F:30])[F:31])[CH:23]=4)[C:9]=3[N:32]=2)[CH2:2][CH2:3]1

Participants

5

Reactant 4

HCID 3776IsopropanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 49779959HCID 49779959, compound

Product 1

HCID 57664251HCID 57664251, compound

Conditions

Temperature
95 °C

Procedure

3-(cyclopropylamino)-5-(3-(trifluoromethyl)phenylamino)pyrimido[4,5-c]quinoline-8-carboxylic acid (100 mg, 0.23 mmol) was reacted with diphenylphosphoryl azide (50 ul, 0.23 mmol) and triethylamine (34 ul, 0.23 mmol) in isopropanol (8 ml). The mixture was stirred at 95° C. for 3 hours. The solvents were removed and the residue partitioned between water and ethylacetate. The organic layer was dried over Na2SO4 and the solvents removed in vacuo. Addition of CH2Cl2 induced formation of a solid that was filtered off and dried to afford isopropyl 3-(cyclopropylamino)-5-(3-(trifluoromethyl)phenylamino)pyrimido[4,5-c]quinolin-8-ylcarbamate. LCMS (ES): 90% pure, m/z 497 [M+1]+.

Workup

  1. customThe solvents were removed
  2. customthe residue partitioned between water and ethylacetate
  3. dry with materialThe organic layer was dried over Na2SO4
  4. customthe solvents removed in vacuo
  5. additionAddition of CH2Cl2 induced formation of a solid
  6. filtrationthat was filtered off
  7. customdried

Sources & evidence

ORD record
ord-d28b3d72db094ad1b29b744fd3477702
Source dataset
uspto-grants-2012_05
Patent number
US08168651B2

Reaction notes

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