Methylamine → HCID 86613178, compound

HRID 746801Notes

Reaction equation

HRID 746801 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[S:16][CH:17]=[CH:18][C:19]=3[NH:20][S:21]([CH:24]([CH3:26])[CH3:25])(=[O:23])=[O:22])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1)=O.[CH3:27][NH2:28].C1COCC1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl>[CH3:27][NH:28][CH2:1][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[S:16][CH:17]=[CH:18][C:19]=3[NH:20][S:21]([CH:24]([CH3:26])[CH3:25])(=[O:23])=[O:22])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 6329MethylamineHCID 8028TetrahydrofuranHCID 5049666Sodium triacetoxyborohydrideHCID 86613179HCID 86613179, compound

Product 1

HCID 86613178HCID 86613178, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Mix propane-2-sulfonic acid [2-(4′-formyl-biphenyl-4-yl)-thiophen-3-yl]-amide (0.16 mmol) in 1,2-dichloroethane (2 ml) and add methylamine 2N in THF (0.16 ml, 0.32 mmol) at room temperature. Stir the resulting solution for 5 min before adding Na(OAc)3BH (0.32 mmol). Stir the mixture at room temperature for 16 h. Analyze by LC/MS for final product. Add saturated NaHCO3 aqueous solution and dichloromethane and filter the mixture through hydrophobic filter. Evaporate the filtrate and apply the residue to SCX cartridge, elute with MeOH/DCM to remove non-basic materials, followed by 2N NH3 in MeOH to give a crude product. Purify by flash chromatography (Silica gel-Dichloromethane/Methanol 7:1)to yield the title compound. MS (ES−): 399(M−1).

Workup

  1. stirringStir the mixture at room temperature for 16 h

Sources & evidence

ORD record
ord-fbf89e56b4fd478387d267d626551943
Source dataset
uspto-grants-2008_07
Patent number
US07393868B2

Reaction notes

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