(2S)-2-Amino-N,3,3-trimethylbutanamide → (S)-5-Cyclopropyl-N-(3,3-dimethyl-1-(methylamino)-1-oxobutan-2-yl)-6-((tetrahydro-2H-pyran-4-yl)methoxy)picolinamide

HRID 632259Notes

Reaction equation

HRID 632259 reaction equation
[CH:1]1([C:4]2[CH:5]=[CH:6][C:7]([C:18]([OH:20])=O)=[N:8][C:9]=2[O:10][CH2:11][CH:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[CH2:3][CH2:2]1.C1(C2C=CC(C(O)=O)=NC=2OCC2CCCO2)CC1.[NH2:40][C@@H:41]([C:46]([CH3:49])([CH3:48])[CH3:47])[C:42]([NH:44][CH3:45])=[O:43]>>[CH:1]1([C:4]2[CH:5]=[CH:6][C:7]([C:18]([NH:40][C@@H:41]([C:46]([CH3:49])([CH3:48])[CH3:47])[C:42]([NH:44][CH3:45])=[O:43])=[O:20])=[N:8][C:9]=2[O:10][CH2:11][CH:12]2[CH2:13][CH2:14][O:15][CH2:16][CH2:17]2)[CH2:2][CH2:3]1

Participants

4

Reactant 3

HCID 445856(2S)-2-Amino-N,3,3-trimethylbutanamideHCID 710872545-Cyclopropyl-6-(tetrahydro-furan-2-ylmethoxy)-pyridine-2-carboxylic acidHCID 710875605-Cyclopropyl-6-(tetrahydro-pyran-4-ylmethoxy)-pyridine-2-carboxylic acid

Product 1

HCID 71087532(S)-5-Cyclopropyl-N-(3,3-dimethyl-1-(methylamino)-1-oxobutan-2-yl)-6-((tetrahydro-2H-pyran-4-yl)methoxy)picolinamide

Procedure

The title compound was synthesized in analogy to Example 1, using 5-cyclopropyl-6-(tetrahydro-pyran-4-ylmethoxy)-pyridine-2-carboxylic acid (which can e.g. be prepared in a similar manner than 5-cyclopropyl-6-(tetrahydro-furan-2-ylmethoxy)-pyridine-2-carboxylic acid (Example 166 b)) and (2S)-2-amino-N,3,3-trimethyl-butanamide (CAN 89226-12-0) as starting materials, MS (EI): m/e=404.3 [M+H]+.

Sources & evidence

ORD record
ord-df0a0f3cde304a65affc715eb580d628
Source dataset
uspto-grants-2016_04
Patent number
US09321727B2

Reaction notes

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