Diisopropylethylamine → 6-Cyclopropylmethoxy-5-(3,3-difluoro-azetidin-1-yl)-pyridine-2-carboxylic acid tert-butyl-ethyl-amide

HRID 624857Notes

Reaction equation

HRID 624857 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.[CH2:21]([NH:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH3:22].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C>>[C:24]([N:23]([CH2:21][CH3:22])[C:12]([C:10]1[CH:9]=[CH:8][C:7]([N:15]2[CH2:18][C:17]([F:20])([F:19])[CH2:16]2)=[C:6]([O:5][CH2:4][CH:1]2[CH2:2][CH2:3]2)[N:11]=1)=[O:14])([CH3:27])([CH3:26])[CH3:25]

Participants

5

Reactant 4

HCID 81531DiisopropylethylamineHCID 521156N-tert-ButylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 710872926-(Cyclopropylmethoxy)-5-(3,3-difluoroazetidin-1-yl)picolinic acid

Product 1

HCID 902037696-Cyclopropylmethoxy-5-(3,3-difluoro-azetidin-1-yl)-pyridine-2-carboxylic acid tert-butyl-ethyl-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 N-ethyl-2-methylpropan-2-amine (CAN 4432-77-3) in the presence of TBTU and DIEA to give the title compound as colorless oil; MS (EI): m/e=368.5 [MH+].

Sources & evidence

ORD record
ord-870a0d04b6f74c1584268a4641c95975
Source dataset
uspto-grants-2016_04
Patent number
US09303012B2

Reaction notes

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