Diisopropylethylamine → HCID 90215307, compound

HRID 624908Notes

Reaction equation

HRID 624908 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]12[CH2:30][C@H:27]([NH:28][CH2:29]1)[CH2:26][C:25]([CH3:32])([CH3:31])[CH2:24]2.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([CH2:4][O:5][C:6]2[N:11]=[C:10]([C:12]([N:28]3[CH2:29][C@:23]4([CH3:22])[CH2:30][C@H:27]3[CH2:26][C:25]([CH3:32])([CH3:31])[CH2:24]4)=[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

5

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 710872926-(Cyclopropylmethoxy)-5-(3,3-difluoroazetidin-1-yl)picolinic acidHCID 118451448HCID 118451448, compound

Product 1

HCID 90215307HCID 90215307, compound

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 (1S,5R)-1,3,3-trimethyl-6-azabicyclo[3.2.1]octane hydrochloride (380228-03-5) in the presence of TBTU and DIEA to obtain the title compound as colorless oil; MS (EI): m/e=420.2 [MH+].

Sources & evidence

ORD record
ord-8407e9aa48f74527bdf6311cba8ae755
Source dataset
uspto-grants-2016_04
Patent number
US09303012B2

Reaction notes

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