HCID 68810823, compound → HCID 9842488, compound

HRID 1790857Notes

Reaction equation

HRID 1790857 reaction equation
C(OC(=O)[NH:7][CH:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[CH:16][CH:17]=[C:18]3[C:23]=2[N:22]=[C:21]([N:24]2[C:28]4[CH:29]=[CH:30][C:31]([O:33][CH3:34])=[CH:32][C:27]=4[N:26]=[CH:25]2)[CH:20]=[CH:19]3)[CH2:10][CH2:9]1)(C)(C)C>FC(F)(F)C(O)=O>[CH3:34][O:33][C:31]1[CH:30]=[CH:29][C:28]2[N:24]([C:21]3[CH:20]=[CH:19][C:18]4[C:23](=[C:14]([N:11]5[CH2:10][CH2:9][CH:8]([NH2:7])[CH2:13][CH2:12]5)[CH:15]=[CH:16][CH:17]=4)[N:22]=3)[CH:25]=[N:26][C:27]=2[CH:32]=1

Participants

3

Reactant 1

HCID 68810823HCID 68810823, compound

Product 1

HCID 9842488HCID 9842488, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

{1-[2-(5-Methoxy-benzoimidazol-1-yl)-quinolin-8-yl]-piperidin-4-yl}-carbamic acid tert-butyl ester G (8.40 g, 17.7 mmol) was dissolved in 50 mL of trifluoroacetic acid (TFA) under an atmosphere of dry N2. The reaction mixture was stirred at ambient temperature for 15 minutes after which time it was concentrated under vacuum to give a yellow oil. The oil was partitioned between DCM and 0.1N aqueous NaOH. The DCM layer was washed again with 0.1N aqueous NaOH. The DCM layer was dried over Na2SO4, filtered and concentrated to give 5.85 g of 1-[2-(5-Methoxy-benzoimidazol-1-yl)-quinolin-8-yl]-piperidin-4-ylamine as a yellow solid. C.I. m/z 374 [M+1]; 1H NMR (CDCl3) δ 8.66 (s, 1 H), 8.37 (d, J=8.9 Hz, 1 H), 8.30 (d, J=8.7 Hz, 1 H), 7.68 (d, J=8.9 Hz, 1 H), 7.47 (m, 2 H), 7.35 (d, J=2.3 Hz, 1 H), 7.25 (m, 1 H), 7.06 (dd, J=2.5, 8.9 Hz, 1 H), 3.91 (s, 3 H), 3.88 (m, 2 H), 2.90 (m, 3 H), 2.05 (m, 2 H), 1.83 (m, 2 H), 1.50 (brs, 2 H).

Workup

  1. concentrationwas concentrated under vacuum
  2. customto give a yellow oil
  3. customThe oil was partitioned between DCM and 0.1N aqueous NaOH
  4. washThe DCM layer was washed again with 0.1N aqueous NaOH
  5. dry with materialThe DCM layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-067c9c222567442b89d655c5c7c1f3c7
Source dataset
uspto-grants-2006_07
Patent number
US07071337B2

Reaction notes

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