Methanol → HCID 67315208, compound

HRID 1012743Notes

Reaction equation

HRID 1012743 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C([BH3-])#N.[Na+].[ClH:11].[N:12]12[CH2:19][CH2:18][CH:15]([CH2:16][CH2:17]1)[C@@H:14]([NH:20][C:21]([C:23]1[S:24][C:25]3[CH:31]=[C:30]([C:32]4[CH:37]=[CH:36][C:35]([CH:38]=O)=[CH:34][CH:33]=4)[CH:29]=[CH:28][C:26]=3[CH:27]=1)=[O:22])[CH2:13]2.CO>C(O)(=O)C>[ClH:11].[ClH:11].[N:12]12[CH2:17][CH2:16][CH:15]([CH2:18][CH2:19]1)[C@@H:14]([NH:20][C:21]([C:23]1[S:24][C:25]3[CH:31]=[C:30]([C:32]4[CH:33]=[CH:34][C:35]([CH2:38][N:1]5[CH2:6][CH2:5][O:4][CH2:3][CH2:2]5)=[CH:36][CH:37]=4)[CH:29]=[CH:28][C:26]=3[CH:27]=1)=[O:22])[CH2:13]2

Participants

6

Reactant 4

HCID 887MethanolHCID 8083MorpholineHCID 5003444Sodium cyanoborohydrideHCID 86606708HCID 86606708, compound

Product 1

HCID 67315208HCID 67315208, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

330 mg (3.75 mmol) of morpholine and 40 mg (0.56 mmol) of sodium cyanoborohydride are successively added to a solution of 80 mg (0.19 mmol) of 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-4f2b3f9f24ca4701bb8431f39b271814
Source dataset
uspto-grants-2011_07
Patent number
US07977485B2

Reaction notes

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