Isopropylamine → HCID 70145486, compound

HRID 1281694Notes

Reaction equation

HRID 1281694 reaction equation
[CH:1]([NH2:4])([CH3:3])[CH3:2].Br[C:6]1[N:10]([C@@H:11]2[CH2:16][CH2:15][C@@H:14]([OH:17])[C@@H:13]([OH:18])[CH2:12]2)[C:9]2[CH:19]=[C:20]([Cl:24])[C:21]([Cl:23])=[CH:22][C:8]=2[N:7]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[CH:1]([NH:4][C:6]1[N:10]([C@@H:11]2[CH2:16][CH2:15][C@@H:14]([OH:17])[C@@H:13]([OH:18])[CH2:12]2)[C:9]2[CH:19]=[C:20]([Cl:24])[C:21]([Cl:23])=[CH:22][C:8]=2[N:7]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6363IsopropylamineHCID 10340Sodium CarbonateHCID 57309427HCID 57309427, compound

Product 1

HCID 70145486HCID 70145486, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

Isopropylamine (99.5 mg, 1.68 mmol) was added to (±)-(1R*,2S*,4R*)-4-(2-bromo-5,6-dichloro-1H-benzimidazol-1-yl)cyclohexane-1,2-diol (Example 49, part g, 64.0 mg, 168.4 mmol) in ethanol (3.4 ml) and the reaction was heated at 100° C. in a sealed tube for 67 hr. The reaction was cooled, saturated sodium carbonate added, extracted with ethyl acetate, dried with magnesium sulfate, and concentrated. The residue was purified by column chromatography eluting with methanol:ethyl acetate (1:19) to give the title compound (47.9 mg, 79%). Rf=0.24 (1:19 methanol:ethyl acetate); 1H-NMR (CD3OD, 300 MHz) δ7.46 (s, 1H), 7.31 (s, 1H), 4.44 (tt, 1H, J=13, 4), 4.11 (s, 1H), 4.05 (h, 1H, J=7), 3.82 (dt, 1H, J=10,4), 2.41 (dt, 1H, J=13,2), 2.26 (dq, 1H, J=13,4), 2.04-1.75 (m, 4H), 1.29 (d, 6H, J=6); MS (ES) M+H=358.

Workup

  1. temperatureThe reaction was cooled
  2. extractionextracted with ethyl acetate
  3. dry with materialdried with magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography
  6. washeluting with methanol:ethyl acetate (1:19)

Sources & evidence

ORD record
ord-577586f9a8534c2d9a6b8d1a48709ad7
Source dataset
uspto-grants-2002_09
Patent number
US06455507B1

Reaction notes

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