Methanol → HCID 67315208, compound

HRID 2179617Notes

Reaction equation

HRID 2179617 reaction equation
[ClH:1].[N:2]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[C@@H:4]([NH:10][C:11]([C:13]1[S:14][C:15]3[CH:21]=[C:20]([C:22]4[CH:27]=[CH:26][C:25](C=O)=[CH:24][CH:23]=4)[CH:19]=[CH:18][C:16]=3[CH:17]=1)=[O:12])[CH2:3]2.[CH3:30][OH:31]>C(O)(=O)C>[ClH:1].[ClH:1].[N:2]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[C@@H:4]([NH:10][C:11]([C:13]1[S:14][C:15]3[CH:21]=[C:20]([C:22]4[CH:23]=[CH:24][C:25]([CH2:7][N:2]5[CH2:3][CH2:4][O:31][CH2:30][CH2:9]5)=[CH:26][CH:27]=4)[CH:19]=[CH:18][C:16]=3[CH:17]=1)=[O:12])[CH2:3]2

Participants

4

Reactant 2

HCID 887MethanolHCID 86606708HCID 86606708, compound

Product 1

HCID 67315208HCID 67315208, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-6-(4-formylphenyl)-1-benzothiophene-2-carboxamide hydrochloride (Example 23A) in 1.5 ml of a 6:1 mixture of methanol and acetic acid. 2 h at room temperature and 6 h at 80° C. are followed by purification by preparative HPLC. The product fractions are concentrated and, after addition of a 5:1 mixture of methanol and 1N hydrochloric acid, again concentrated. Drying under high vacuum results in 87.7 mg (88% of theory) of the title compound.

Workup

  1. custom2 h at room temperature and 6 h at 80° C. are followed by purification by preparative HPLC
  2. concentrationThe product fractions are concentrated
  3. additionafter addition of a 5:1 mixture of methanol and 1N hydrochloric acid
  4. concentrationagain concentrated
  5. customDrying under high vacuum

Sources & evidence

ORD record
ord-9092dd928c3245c9864c7b5c0f5607e4
Source dataset
uspto-grants-2015_06
Patent number
US09067931B2

Reaction notes

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