Methanol → HCID 67313610, compound

HRID 2179723Notes

Reaction equation

HRID 2179723 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][CH:35]=[C:34]([CH:38]=O)[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:37]=[CH:36][CH:35]=[C:34]([CH2:38][N:1]5[CH2:6][CH2:5][O:4][CH2:3][CH2:2]5)[CH:33]=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 86606711HCID 86606711, compound

Product 1

HCID 67313610HCID 67313610, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

290 mg (3.32 mmol) of morpholine and 31 mg (0.50 mmol) of sodium cyanoborohydride are successively added to a solution of 80 mg (0.17 mmol) of N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-6-(3-formylphenyl)-1-benzothiophene-2-carboxamide hydrochloride (Example 33A) in 1.0 ml of a 6:1 mixture of methanol and acetic acid. After 18 h at. 80° C., purification is carried out by preparative HPLC.

Workup

  1. custom80° C., purification

Sources & evidence

ORD record
ord-f7cfeff1999d47c784523a705e57b35b
Source dataset
uspto-grants-2015_06
Patent number
US09067931B2

Reaction notes

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