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Sodium Bicarbonate → 2-(2-Methoxyphenyl)-5,6,7,8-tetrahydro-8-(2-((triphenylmethyl)thio)ethyl)-imidazo[1,2-a]pyrazine

HRID 901125
Notes
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Reaction equation

HRID 901125 reaction equation
CC(C)(OC([N:7]1[CH2:12][CH2:11][N:10]2[CH:13]=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[O:22][CH3:23])[N:15]=[C:9]2[CH:8]1[CH2:24][CH2:25][S:26][C:27]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=O)C.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:23][O:22][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[C:14]1[N:15]=[C:9]2[CH:8]([CH2:24][CH2:25][S:26][C:27]([C:40]3[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=3)([C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[NH:7][CH2:12][CH2:11][N:10]2[CH:13]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 220168347-((1,1-Dimethylethoxy)carbonyl)-2-(2-methoxyphenyl)-5,6,7,8-tetrahydro-8-(2-((triphenylmethyl)thio)ethyl)-imidazo[1,2-a]pyrazine

Product 1

HCID 220168072-(2-Methoxyphenyl)-5,6,7,8-tetrahydro-8-(2-((triphenylmethyl)thio)ethyl)-imidazo[1,2-a]pyrazineYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product from Step 13.f. (2.50 g, 3.96 mmol) was dissolved in CH2Cl2 (16.0 ml) and treated with Tfa (4.0 ml) at room temperature under N2 for about 3.5 hours. The reaction was then poured cautiously into a saturated NaHCO3 solution (150 ml) and the product was extracted with CH2Cl2 (2×50 ml), dried over Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified by flash chromatography on silica gel using 9:1/ hexanes:EtOAc and then 100% EtOAc as eluants. Product fractions were combined and concentrated under reduced pressure to obtain a white foam (1.35 g, 64%) which was used without further purification. Mass spec. 532.4 MH+.

Workup

  1. additiontreated with Tfa (4.0 ml) at room temperature under N2 for about 3.5 hours
  2. extractionthe product was extracted with CH2Cl2 (2×50 ml)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by flash chromatography on silica gel using 9:1/ hexanes
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-93c86ffc4751460e9b9d90e710803252
Source dataset
uspto-grants-2008_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07361656B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes