6-(Cyclopropylmethoxy)-5-(3,3-difluoroazetidin-1-yl)picolinic acid → 6-Cyclopropylmethoxy-5-(3,3-difluoro-azetidin-1-yl)-pyridine-2-carboxylic acid ((S)-1-cyclopropylmethyl-2-hydroxy-2-methyl-propyl)-amide

HRID 632173Notes

Reaction equation

HRID 632173 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.[NH2:21][C@@H:22]([CH2:27][CH:28]1[CH2:30][CH2:29]1)[C:23]([CH3:26])([OH:25])[CH3:24]>>[CH:28]1([CH2:27][C@H:22]([NH:21][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])[C:23]([OH:25])([CH3:26])[CH3:24])[CH2:30][CH2:29]1

Participants

3

Reactant 2

HCID 710872926-(Cyclopropylmethoxy)-5-(3,3-difluoroazetidin-1-yl)picolinic acidHCID 86674766(S)-3-Amino-4-cyclopropyl-2-methyl-butan-2-ol

Product 1

HCID 711056156-Cyclopropylmethoxy-5-(3,3-difluoro-azetidin-1-yl)-pyridine-2-carboxylic acid ((S)-1-cyclopropylmethyl-2-hydroxy-2-methyl-propyl)-amide

Procedure

The title compound was synthesized in analogy to Example 1, using 6-cyclopropylmethoxy-5-(3,3-difluoro-azetidin-1-yl)-pyridine-2-carboxylic acid (Example 69 b) and (S)-3-amino-4-cyclopropyl-2-methyl-butan-2-ol as starting materials, MS (EI): m/e=410.2 [M+H]+.

Sources & evidence

ORD record
ord-c07f8a761e624862ba55f133603ed0f2
Source dataset
uspto-grants-2016_04
Patent number
US09321727B2

Reaction notes

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