HCID 71268695, compound → HCID 60197784, compound

HRID 1630616Notes

Reaction equation

HRID 1630616 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([CH2:11][CH:12]([C:14]3[N:15](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[CH:16]=[CH:17][N:18]=3)[OH:13])[C:6]3[CH2:38][CH2:39][N:40]4[CH:44]([C:5]=3[C:4]=2[CH:3]=1)[CH2:43][CH2:42][CH2:41]4>CO.Cl>[NH:15]1[CH:16]=[CH:17][N:18]=[C:14]1[CH:12]([OH:13])[CH2:11][N:7]1[C:8]2[CH:9]=[CH:10][C:2]([CH3:1])=[CH:3][C:4]=2[C:5]2[CH:44]3[N:40]([CH2:39][CH2:38][C:6]1=2)[CH2:41][CH2:42][CH2:43]3

Participants

4

Reactant 1

HCID 71268695HCID 71268695, compound

Product 1

HCID 60197784HCID 60197784, compoundYield 4.9%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

A suspension of 2-(10-methyl-2,3,5,6-tetrahydro-1H-indolizino[7,8-b]indol-7(11cH)-yl)-1-(1-trityl-1H-imidazol-2-yl)ethanol (0.4 g, 0.69 mmol) in MeOH (10 mL), 1N HCl (1 mL) was added and the reaction mixture was stirred at RT for 2 h. The reaction mixture concentrated under vacuum to obtain the crude product that was basified with satd. sodium bicarbonate solution and extracted with EtOAc (50 mL). The organic layer was dried over anhydrous sodium sulfate, and concentrated under vacuum to obtain the crude product, which was purified by reverse HPLC to obtain 11.30 mg 1-(1H-imidazol-2-yl)-2-(10-methyl-2,3,5,6-tetrahydro-1H-indolizino[7,8-b]indol-7(11cH)-yl)ethanol. 1H NMR (CD3OD, TFA salt) δ (ppm): 7.44 (s, 2H), 7.27 (s, 1H), 7.13 (d, 1H), 6.99 (d, 1H), 5.37 (t, 1H), 5.1 (m, 1H),4.56 (dd, 1H), 4.46 (dd, 1H), 3.67 (m, 3H), 3.42 (m, 1H), 3.24 (m, 2H), 2.7 (m, 1H), 2.4 (s, 3H), 2.2 (m, 3H).

Workup

  1. additionwas added
  2. concentrationThe reaction mixture concentrated under vacuum
  3. customto obtain the crude product that
  4. extractionsodium bicarbonate solution and extracted with EtOAc (50 mL)
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated under vacuum
  7. customto obtain the crude product, which
  8. customwas purified by reverse HPLC

Sources & evidence

ORD record
ord-1010581805dc4816abb4a1a58d95c5d4
Source dataset
uspto-grants-2014_07
Patent number
US08791132B2

Reaction notes

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