Diisopropylethylamine → 6-Cyclopropylmethoxy-5-(3,3-difluoro-azetidin-1-yl)-pyridine-2-carboxylic acid cyclopropylmethyl-methyl-amide

HRID 624966Notes

Reaction equation

HRID 624966 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.[CH:22]1([CH2:25][NH:26][CH3:27])[CH2:24][CH2:23]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:22]1([CH2:25][N:26]([CH3:27])[C:12]([C:10]2[CH:9]=[CH:8][C:7]([N:15]3[CH2:18][C:17]([F:20])([F:19])[CH2:16]3)=[C:6]([O:5][CH2:4][CH:1]3[CH2:2][CH2:3]3)[N:11]=2)=[O:14])[CH2:24][CH2:23]1

Participants

5

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 12919210(Cyclopropylmethyl)(methyl)amine hydrochlorideHCID 710872926-(Cyclopropylmethoxy)-5-(3,3-difluoroazetidin-1-yl)picolinic acid

Product 1

HCID 762810666-Cyclopropylmethoxy-5-(3,3-difluoro-azetidin-1-yl)-pyridine-2-carboxylic acid cyclopropylmethyl-methyl-amide

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 1-cyclopropyl-N-methylmethanamine hydrochloride (77335-18-3) in the presence of TBTU and DIEA to obtain the title compound as colorless oil; MS (EI): m/e=352.4 [MH+].

Sources & evidence

ORD record
ord-19174b6a8bd0481e8c40dab7b687a7c1
Source dataset
uspto-grants-2016_04
Patent number
US09303012B2

Reaction notes

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