Diisopropylethylamine → [5-Cyclopropyl-6-(2-methyl-propane-1-sulfonyl)-pyridin-2-yl]-(2,2-dimethyl-pyrrolidin-1-yl)-methanone

HRID 624883

Reaction equation

HRID 624883 reaction equation
[CH:1]1([C:4]2[CH:5]=[CH:6][C:7]([C:17]([OH:19])=O)=[N:8][C:9]=2[S:10]([CH2:13][CH:14]([CH3:16])[CH3:15])(=[O:12])=[O:11])[CH2:3][CH2:2]1.[CH3:20][C:21]1([CH3:26])[CH2:25][CH2:24][CH2:23][NH:22]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C>>[CH:1]1([C:4]2[CH:5]=[CH:6][C:7]([C:17]([N:22]3[CH2:23][CH2:24][CH2:25][C:21]3([CH3:26])[CH3:20])=[O:19])=[N:8][C:9]=2[S:10]([CH2:13][CH:14]([CH3:15])[CH3:16])(=[O:11])=[O:12])[CH2:2][CH2:3]1

Participants

5

Reactant 4

HCID 81531DiisopropylethylamineHCID 4147732,2-DimethylpyrrolidineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 710877315-Cyclopropyl-6-(isobutylsulfonyl)picolinic acid

Product 1

HCID 90203535[5-Cyclopropyl-6-(2-methyl-propane-1-sulfonyl)-pyridin-2-yl]-(2,2-dimethyl-pyrrolidin-1-yl)-methanone

Procedure

In analogy to the procedure described in Example 47 b), 5-cyclopropyl-6-(isobutylsulfonyl)picolinic acid (Example 6 d)) was reacted with 2,2-dimethylpyrrolidine (CAN 35018-15-6) in the presence of TBTU and DIEA to obtain the title compound as colorless solid; MS (EI): m/e=365.5 [MH+].

Sources & evidence

ORD record
ord-73115601f6cb488ea1fb63a0ae8beea3
Source dataset
uspto-grants-2016_04
Patent number
US09303012B2

Linked notes

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