Sodium Carbonate → 1-[8-(4-Amino-piperidin-1-yl)-quinolin-2-yl]-1H-benzoimidazol-5-ol

HRID 1790858Notes

Reaction equation

HRID 1790858 reaction equation
C[O:2][C:3]1[CH:28]=[CH:27][C:6]2[N:7]([C:10]3[CH:19]=[CH:18][C:17]4[C:12](=[C:13]([N:20]5[CH2:25][CH2:24][CH:23]([NH2:26])[CH2:22][CH2:21]5)[CH:14]=[CH:15][CH:16]=4)[N:11]=3)[CH:8]=[N:9][C:5]=2[CH:4]=1.B(Br)(Br)Br.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl>[NH2:26][CH:23]1[CH2:24][CH2:25][N:20]([C:13]2[CH:14]=[CH:15][CH:16]=[C:17]3[C:12]=2[N:11]=[C:10]([N:7]2[C:6]4[CH:27]=[CH:28][C:3]([OH:2])=[CH:4][C:5]=4[N:9]=[CH:8]2)[CH:19]=[CH:18]3)[CH2:21][CH2:22]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 25134Boron tribromideHCID 9842488HCID 9842488, compound

Product 1

HCID 99250031-[8-(4-Amino-piperidin-1-yl)-quinolin-2-yl]-1H-benzoimidazol-5-ol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-[2-(5-Methoxy-benzoimidazol-1-yl)-quinolin-8-yl]-piperidin-4-ylamine (500 mg, 1.10 mmol) was dissolved in 10 mL of DCM under an atmosphere of dry N2. To this solution was added boron tribromide (300 mL, 3.30 mmol) and the mixture was stirred overnight at ambient temperature. Then an additional 200 mL of borontribromide was added and the mixture was stirred for two hours. The reaction mixture was then poured over crushed ice and the pH of the resulting solution was adjusted to 9 with the careful addition of sodium carbonate (Na2CO3). The slurry was filtered and the solid was washed with water followed by Et2O and then dried under vacuum to give 1-[8-(4-Amino-piperidin-1-yl)-quinolin-2-yl]-1H-benzoimidazol-5-ol as a yellow solid. C.I. m/z 360 [M+1]; 1H NMR (DMSO) δ 9.07 (s, 1 H), 8.76 (d, J=8.9 Hz, 1 H), 8.48 (d, J=8.9 Hz, 1 H), 8.10 (d, J=8.9 Hz, 1 H), 7.56 (d, J=7.4 Hz, 1 ), 7.45 (m, 1 H), 7.26 (d, J=7.4 Hz, 1 H), 7.01 (d, J=2.2 Hz, 1 H), 6.95 (dd, J=2.2, 8.9 Hz, 1 H), 3.72 (m, 2 H), 2.76 (m, 3 H), 1.88 (m, 2 H), 1.65 (m, 2 H).

Workup

  1. additionThen an additional 200 mL of borontribromide was added
  2. stirringthe mixture was stirred for two hours
  3. additionThe reaction mixture was then poured
  4. customover crushed ice
  5. filtrationThe slurry was filtered
  6. washthe solid was washed with water
  7. customdried under vacuum

Sources & evidence

ORD record
ord-257b8285598045b99878fc22fb33fe10
Source dataset
uspto-grants-2006_07
Patent number
US07071337B2

Reaction notes

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