Ethyl Acetate → HCID 178422922, compound

HRID 1672483Notes

Reaction equation

HRID 1672483 reaction equation
C[O:2][C:3]1[C:4]([CH3:21])=[CH:5][CH:6]=[C:7]2[C:12]=1[N:11]=[C:10]([NH:13][C@H:14]1[CH2:19][CH2:18][C@H:17]([OH:20])[CH2:16][CH2:15]1)[N:9]=[CH:8]2.CCOC(C)=O>CN(C=O)C>[OH:20][C@H:17]1[CH2:16][CH2:15][C@H:14]([NH:13][C:10]2[N:9]=[CH:8][C:7]3[C:12](=[C:3]([OH:2])[C:4]([CH3:21])=[CH:5][CH:6]=3)[N:11]=2)[CH2:19][CH2:18]1

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 178489836HCID 178489836, compound

Product 1

HCID 178422922HCID 178422922, compoundYield 95.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of trans-4-[(8-methoxy-7-methylquinazolin-2-yl)amino]cyclohexanol (16.7 g, 0.058 mol) in DMF (280 mL) was added NaSEt (11.9 g, 0.142 mol) in one portion at room temperature. The reaction mixture was stirred at 120° C. for 3 h. TLC (EtOAc) indicated the reaction was complete. DMF was removed in vacuo. The residue was taken up with water (200 mL), and the aqueous solution was adjusted to pH 6 with 1 N aq. HCl. The precipitate was filtered, washed with water (60 mL×2) and dried in vacuo to give the title compound (15.1 g, 95%) as an off-white solid.

Workup

  1. customDMF was removed in vacuo
  2. filtrationThe precipitate was filtered
  3. washwashed with water (60 mL×2)
  4. customdried in vacuo

Sources & evidence

ORD record
ord-9a890d1181a442758765362d81d5002c
Source dataset
uspto-grants-2011_08
Patent number
US07998978B2

Reaction notes

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