Diisopropylethylamine → HCID 76280805, compound

HRID 624938Notes

Reaction equation

HRID 624938 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[N:11]=[C:10]([C:12]([OH:14])=O)[CH:9]=[CH:8][C:7]=2[N:15]2[CH2:18][C:17]([F:20])([F:19])[CH2:16]2)[CH2:3][CH2:2]1.Cl.[CH3:22][C:23]1([CH3:31])[CH2:27][NH:26][CH:25]([C:28]([NH2:30])=[O:29])[CH2:24]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C>CS(C)=O>[CH:1]1([CH2:4][O:5][C:6]2[N:11]=[C:10]([C:12]([N:26]3[CH2:27][C:23]([CH3:31])([CH3:22])[CH2:24][CH:25]3[C:28]([NH2:30])=[O:29])=[O:14])[CH:9]=[CH:8][C:7]=2[N:15]2[CH2:18][C:17]([F:20])([F:19])[CH2:16]2)[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 710872926-(Cyclopropylmethoxy)-5-(3,3-difluoroazetidin-1-yl)picolinic acidHCID 90203546HCID 90203546, compound

Product 1

HCID 76280805HCID 76280805, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

In analogy to the procedure described in Example 47 b), 6-cyclopropylmethoxy-5-(3,3-difluoro-azetidin-1-yl)-pyridine-2-carboxylic acid (Example 1 b)) was reacted with 4,4-dimethylpyrrolidine-2-carboxamide hydrochloride (Example 90 d) in the presence of TBTU and DIEA. The mixture of enantiomers was separated by chiral HPLC (Reprosil Chiral NR). The (−) enantiomer was isolated as yellow solid; MS (EI): m/e=409.6 [MH+]; αD20 (DMSO)=−29.3°.

Workup

  1. additionThe mixture of enantiomers
  2. customwas separated by chiral HPLC (Reprosil Chiral NR)
  3. customThe (−) enantiomer was isolated as yellow solid

Sources & evidence

ORD record
ord-38f7e0cae3d049b6ad07e073510f6e38
Source dataset
uspto-grants-2016_04
Patent number
US09303012B2

Reaction notes

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