Dimethylformamide → HCID 24967422, compound

HRID 1162768Notes

Reaction equation

HRID 1162768 reaction equation
[C:1]([C:5]1[C:9]([CH:10]=O)=[CH:8][N:7]([CH2:12][C:13]([NH:15][C:16]2[S:20][C:19]3[CH2:21][CH2:22][CH2:23][CH2:24][C:18]=3[C:17]=2[C:25]([NH2:27])=[O:26])=[O:14])[N:6]=1)([CH3:4])([CH3:3])[CH3:2].Cl.[CH3:29][NH:30][CH3:31].CN(C=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(O)(=O)C>[C:1]([C:5]1[C:9]([CH2:10][N:30]([CH3:31])[CH3:29])=[CH:8][N:7]([CH2:12][C:13]([NH:15][C:16]2[S:20][C:19]3[CH2:21][CH2:22][CH2:23][CH2:24][C:18]=3[C:17]=2[C:25]([NH2:27])=[O:26])=[O:14])[N:6]=1)([CH3:3])([CH3:2])[CH3:4]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10473Dimethylamine, hydrochlorideHCID 5049666Sodium triacetoxyborohydrideHCID 59520484HCID 59520484, compound

Product 1

HCID 24967422HCID 24967422, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2-[2-(3-Tert-butyl-4-formylpyrazol-1-yl)-acetylamino]-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide (50 mg, 0.13 mmol) and dimethylamine hydrochloride (20 mg, 0.23 mmol) were mixed with DMF (0.3 mL) and acetic acid (0.3 mL). Sodium triacetoxyborohydride (70 mg, 0.33 mmol) was added and the mixture stirred for 1 h. The reaction was quenched with MeOH and water and directly purified by preparative reverse phase HPLC. The clean product was passed down an SCX cartridge and the volatiles were blown off under a nitrogen atmosphere (2.1 mg, 5 μmol, 4%).

Workup

  1. customThe reaction was quenched with MeOH and water
  2. customdirectly purified by preparative reverse phase HPLC

Sources & evidence

ORD record
ord-80a1ec3c006340cd805c90c5f84f697d
Source dataset
uspto-grants-2010_10
Patent number
US07820707B2

Reaction notes

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