Sodium Bicarbonate → HCID 71007537, compound

HRID 2408719Notes

Reaction equation

HRID 2408719 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([CH2:11][CH:12]([C:14]3[N:18](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[CH:17]=[N:16][CH:15]=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.C(=O)(O)[O-].[Na+]>CO.Cl>[NH:18]1[C:14]([CH:12]([OH:13])[CH2:11][N:7]2[C:8]3[CH:9]=[CH:10][C:2]([CH3:1])=[CH:3][C:4]=3[C:5]3[CH:44]4[N:40]([CH2:39][CH2:38][C:6]2=3)[CH2:41][CH2:42][CH2:43]4)=[CH:15][N:16]=[CH:17]1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 71268624HCID 71268624, compound

Product 1

HCID 71007537HCID 71007537, compoundYield 5.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

To a stirred solution of compound 2-(10-methyl-2,3,5,6-tetrahydro-1H-indolizino[7,8-b]indol-7(11cH)-yl)-1-(1-trityl-1H-imidazol-5-yl)ethanol (400 mg, 0.69 mmol) in MeOH (10 mL), 1N HCl (1 mL) at 0° C. was added. 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 sat sodium bicarbonate solution and extracted with EtOAc (50 mL). The organic layer dried on anhydrous sodium sulfate, and concentrated under vacuum to obtain the crude product that was purified by reverse phase HPLC to obtain 1-(1H-imidazol-5-yl)-2-(10-methyl-2,3,5,6-tetrahydro-1H-indolizino[7,8-b]indol-7(11cH)-yl)ethanol (12 mg) as the TFA salt. 1H NMR (CD3OD, TFA salt) δ (ppm): 8.79 (s, 1H), 7.4 (s, 1H), 7.27 (s, 1H), 7.2 (dd, 1H), 7.01 (d, 1H), 5.18 (t, 1H), 5.04 (m, 1H), 4.39 (m, 2H), 3.67 (m, 3H), 3.42 (m, 2H), 3.2 (m, 1H), 2.7 (m, 1H), 2.4 (s, 3H), 2.2 (m, 3H). Separation by chiral HPLC provides diastereomers II-140a-d.

Workup

  1. concentrationThe reaction mixture concentrated under vacuum
  2. customto obtain the crude product that
  3. extractionextracted with EtOAc (50 mL)
  4. dry with materialThe organic layer dried on anhydrous sodium sulfate
  5. concentrationconcentrated under vacuum
  6. customto obtain the crude product that
  7. customwas purified by reverse phase HPLC

Sources & evidence

ORD record
ord-59b12893f4e94d58bacc60c2fd877c20
Source dataset
uspto-grants-2014_08
Patent number
US08815843B2

Reaction notes

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