HCID 178504927, compound → HCID 178504934, compound

HRID 1672467Notes

Reaction equation

HRID 1672467 reaction equation
[CH3:1][S:2]([N:5]1[CH2:9][CH2:8][C:7]([C:10]2[CH:11]=[CH:12][CH:13]=[C:14]3[C:19]=2[N:18]=[C:17]([NH:20][C@H:21]2[CH2:26][CH2:25][C@H:24]([OH:27])[CH2:23][CH2:22]2)[N:16]=[CH:15]3)=[CH:6]1)(=[O:4])=[O:3]>CO.[Pd]>[CH3:1][S:2]([N:5]1[CH2:9][CH2:8][CH:7]([C:10]2[CH:11]=[CH:12][CH:13]=[C:14]3[C:19]=2[N:18]=[C:17]([NH:20][C@H:21]2[CH2:26][CH2:25][C@H:24]([OH:27])[CH2:23][CH2:22]2)[N:16]=[CH:15]3)[CH2:6]1)(=[O:3])=[O:4]

Participants

4

Reactant 1

HCID 178504927HCID 178504927, compound

Product 1

HCID 178504934HCID 178504934, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To the solution of trans-4-({8-[1-(methylsulfonyl)-4,5-dihydro-1H-pyrrol-3-yl]quinazolin-2-yl}amino)cyclohexanol (88 mg, 0.23 mmol) in methanol (8 mL) was added 20 mg of Pd/C (dry, 10%). The mixture was hydrogenated with a H2 balloon at RT for 48 h. The catalyst was filtered off and washed with methanol (15 mL). The filtrate was concentrated in vacuo, and the residue was purified by chromatography (eluting with DCM, then DCM/EA=2/1) to give the title compound as off white solid (52 mg, 62%). 1H-NMR (CDCl3, 400 MHz): δ 8.97 (s, 1H), 7.61 (d, J=7.6 Hz, 1H), 7.59 (d, J=7.6 Hz, 1H), 7.21 (dd, J=7.6, 7.6 Hz, 1H), 5.17 (d, J=6.8 Hz, 1H), 4.30-4.25 (m, 1H), 4.01 (dd, J=9.2, 7.6 Hz, 1H), 4.01-3.98 (m, 1H), 3.71-3.67 (m, 2H), 3.54-3.50 (m, 1H), 2.92 (s, 3H), 2.49-2.29 (m, 2H), 2.28-2.24 (m, 2H), 2.12-2.06 (m, 2H), 1.57-1.50 (m, 2H), 1.45-1.30 (m, 2H). MS (m/e) 391.3 (M+1).

Workup

  1. filtrationThe catalyst was filtered off
  2. washwashed with methanol (15 mL)
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe residue was purified by chromatography (
  5. washeluting with DCM

Sources & evidence

ORD record
ord-342cab40baa94b6889c34ab769133156
Source dataset
uspto-grants-2011_08
Patent number
US07998978B2

Reaction notes

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