Toluene → HCID 67408611, compound

HRID 709877Notes

Reaction equation

HRID 709877 reaction equation
[C:1](=[O:25])([O:3][CH2:4][C@H:5]([C:7]1[N:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH:13]=2)[N:8]=1)[CH3:6])[NH2:2].C1(C)C=CC=CC=1.[O-2].[Mg+2].C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1>CC(C(O)=O)(CC1C=CC=C(CC(C(O)=O)(C)C)C=1)C.CC(C(O)=O)(CC1C=CC=C(CC(C(O)=O)(C)C)C=1)C.[Rh].[Rh].C(Cl)Cl>[CH2:18]([O:17][C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C@:5]1([CH3:6])[CH2:4][O:3][C:1](=[O:25])[NH:2]1)[N:16]=[CH:15]2)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].[C:1](=[O:25])([O:3][CH2:4][C@H:5]([C:7]1[N:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH:13]=2)[N:8]=1)[CH3:6])[NH2:2]

Participants

8

Reactant 4

HCID 1140TolueneHCID 6850729Magnesium monoxideHCID 12217721Iodo benzene diacetateHCID 67408933HCID 67408933, compound

Product 2

HCID 67408611HCID 67408611, compoundYield 15%HCID 67408933HCID 67408933, compound

Reagents, catalysts & solvents 2

HCID 727500082,2'-[1,3-Phenylenebis(methylene)]bis(2-methylpropanoic acid)--rhodium (1/1)CatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

(S)-2-(6-Heptyloxyquinazolin-2-yl)propyl carbamate (14, 350 mg, 0.0010 mol) was dissolved in toluene (20 mL, 0.2 mol), followed by magnesium monoxide (93.9 mg, 0.00233 mol), iodobenzene diacetate (359 mg, 0.00111 mol) and finally Rh2(esp)2 (35 mg, 0.000046 mol). The reaction mixture was then heated at 40° C. for 3 days. DCM was added to the reaction mixture, and the reaction mixture was filtered. The crude mixture was then purified via chromatography (SiO2, 12 g, 0-80% ethyl acetate/hexanes) to give 53 mg of the desired product (15%) and 215.0 mg of 14. 1H NMR (CHLOROFORM-d) δ: 9.27 (s, 1H), 7.90 (d, J=9.3 Hz, 1H), 7.58 (dd, J=9.2, 2.6 Hz, 1H), 7.15 (d, J=2.5 Hz, 1H), 6.19 (br. s., 1H), 5.18 (d, J=8.5 Hz, 1H), 4.49 (d, J=8.8 Hz, 1H), 4.11 (t, J=6.5 Hz, 2H), 1.80-1.97 (m, 2H), 1.76 (s, 3H), 1.21-1.60 (m, 8H), 0.91 (t, J=6.7 Hz, 3H). MS (M+1): 344.30.

Workup

  1. filtrationthe reaction mixture was filtered
  2. customThe crude mixture was then purified via chromatography (SiO2, 12 g, 0-80% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-1d08376c1621486eb01d4d76b73fdd72
Source dataset
uspto-grants-2015_11
Patent number
US09181191B2

Reaction notes

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