1-Hydroxybenzotriazole → [(2R)-1-({2-[(2-furylmethyl)amino]-6-methylpyridin-3-yl}carbonyl)pyrrolidin-2-yl](diphenyl)methanol

HRID 2192783Notes

Reaction equation

HRID 2192783 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][NH:7][C:8]1[N:16]=[C:15]([CH3:17])[CH:14]=[CH:13][C:9]=1[C:10]([OH:12])=O.[C:18]1([C:24]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)([CH:26]2[CH2:30][CH2:29][CH2:28][NH:27]2)[OH:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.C(=O)([O-])O.[Na+]>CN(C=O)C>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][NH:7][C:8]1[C:9]([C:10]([N:27]2[CH2:28][CH2:29][CH2:30][C@@H:26]2[C:24]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[OH:25])=[O:12])=[CH:13][CH:14]=[C:15]([CH3:17])[N:16]=1

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 204386DiphenylprolinolHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 596252852-[(2-Furylmethyl)amino]-6-methylnicotinic acid

Product 1

HCID 59625419[(2R)-1-({2-[(2-furylmethyl)amino]-6-methylpyridin-3-yl}carbonyl)pyrrolidin-2-yl](diphenyl)methanolYield 37.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 2-[(2-furylmethyl)amino]-6-methylnicotinic acid (13.9 mg) and diphenyl(pyrrolidin-2-yl)methanol (18.2 mg) in DMF (1.0 ml) was added a solution of HOBt (9.7 mg) and WSC.HCl (13.8 mg) in DMF (0.5 ml), and the mixture was stirred at room temperature overnight. The reaction mixture was poured into 2% aqueous sodium hydrogen carbonate, the mixture was extracted with ethyl acetate, and the extract was concentrated by a nitrogen gas blower. The residue was subjected to reversed-phase preparative HPLC, and the object fraction was passed through MP-CO3 resin (manufactured by Polymer Laboratories) to remove trifluoroacetic acid. The obtained solution was concentrated by a nitrogen gas blower to give the object compound (10.6 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. concentrationthe extract was concentrated by a nitrogen gas blower
  3. customto remove trifluoroacetic acid
  4. concentrationThe obtained solution was concentrated by a nitrogen gas blower

Sources & evidence

ORD record
ord-a2319b50eb904b528a19adab07556db2
Source dataset
uspto-grants-2012_12
Patent number
US08329691B2

Reaction notes

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