Methanol → HCID 178474993, compound

HRID 1672465Notes

Reaction equation

HRID 1672465 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([O:7][C:8]2[CH:9]=[CH:10][CH:11]=[C:12]3[C:17]=2[N:16]=[C:15]([NH:18][C@H:19]2[CH2:24][CH2:23][C@H:22]([NH2:25])[CH2:21][CH2:20]2)[N:14]=[CH:13]3)[CH2:3][CH2:2]1.[C:26](Cl)(=[O:28])[CH3:27].CCN(CC)CC.CO>C(Cl)Cl>[O:1]1[CH2:2][CH2:3][CH:4]([O:7][C:8]2[CH:9]=[CH:10][CH:11]=[C:12]3[C:17]=2[N:16]=[C:15]([NH:18][C@H:19]2[CH2:24][CH2:23][C@H:22]([NH:25][C:26](=[O:28])[CH3:27])[CH2:21][CH2:20]2)[N:14]=[CH:13]3)[CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 887MethanolHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 178511656HCID 178511656, compound

Product 1

HCID 178474993HCID 178474993, compoundYield 54.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of trans-N-[8-(tetrahydro-2H-pyran-4-yloxy)quinazolin-2-yl]cyclohexane-1,4-diamine (0.3 g, 0.876 mmol) and acetyl chloride (0.0825 g, 1.05 mmol) in CH2Cl2 (10 mL) was added Et3N (0.106 g, 1.05 mmol). The resulting mixture was stirred at room temperature overnight. TLC (DCM:MeOH=10:1) showed the reaction was complete. CH2Cl2 (30 mL) was added to the solution. The solution was washed with H2O (3×20 mL) and brine (30 mL), dried over Na2SO4 and concentrated in vacuo to give crude solid, which was washed with ethyl acetate to give the title compound (0.180 g, 54.5%) as a white solid. 1H NMR (CDCl3, 400 Hz): 8.875 (s, 1H), 7.255 (d, 2H), 7.132 (d, 1H), 7.050 (t, 1H), 5.245 (d, 1H), 5.133 (d, 1H), 4.002 (m, 2H), 3.869 (m, 1H), 3.709 (m, 1H), 3.507 (m, 2H), 2.178 (d, 2H), 1.979 (t, 4H), 1.893 (m, 5H), 1.249 (m, 4H).

Workup

  1. washThe solution was washed with H2O (3×20 mL) and brine (30 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customto give crude solid, which
  5. washwas washed with ethyl acetate

Sources & evidence

ORD record
ord-9eb7569199f1489aac6eeaae7a49ae0e
Source dataset
uspto-grants-2011_08
Patent number
US07998978B2

Reaction notes

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