Sodium ethanethiolate → HCID 178515722, compound

HRID 1672448Notes

Reaction equation

HRID 1672448 reaction equation
C[O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[N:8][C:9]([NH:13][C@H:14]3[CH2:19][CH2:18][C@H:17]([OH:20])[CH2:16][CH2:15]3)=[N:10]2)=[CH:5][CH:4]=1.C([S-])C.[Na+]>CN(C=O)C>[OH:20][C@H:17]1[CH2:16][CH2:15][C@H:14]([NH:13][C:9]2[N:8]=[CH:7][C:6]3[C:11](=[CH:12][C:3]([OH:2])=[CH:4][CH:5]=3)[N:10]=2)[CH2:19][CH2:18]1

Participants

4

Reactant 2

HCID 4459711Sodium ethanethiolateHCID 178487634HCID 178487634, compound

Product 1

HCID 178515722HCID 178515722, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of trans-4-[(7-methoxyquinazolin-2-yl)amino]cyclohexanol (161 mg, 0.583 mmol) in DMF (10 mL) was added sodium ethanethiolate (248 mg, 2.95 mmol) and the mix heated to 110° C. for 16 hours. The reaction was cooled and the residue was purified directly via Biotage F/C eluting with 5-10% MeOH/DCM to afford the title compound as an off-white solid, 120 mg, 78%. 1H NMR (400 MHz, DMSO-D6) δ ppm 10.28 (1H, s) 8.79 (1H, s) 7.57 (1H, d, J=8.59 Hz) 6.96 (1H, d, J=8.08 Hz) 6.54-6.79 (2H, m) 4.54 (1H, d, J=3.54 Hz) 3.74 (1H, d, J=3.28 Hz) 3.38 (1H, s) 1.67-1.93 (4H, m) 1.20-1.39 (4H, m); MS (API+) for C14H17N3O2 m/z 260.2 (M+H)+.

Workup

  1. temperatureThe reaction was cooled
  2. customthe residue was purified directly via Biotage F/C
  3. washeluting with 5-10% MeOH/DCM

Sources & evidence

ORD record
ord-b9c16ce75ab24adf97b22b79517b361d
Source dataset
uspto-grants-2011_08
Patent number
US07998978B2

Reaction notes

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