Leucinamide → 6-Cyclopropylmethoxy-5-(tetrahydro-furan-2-yl)-pyridine-2-carboxylic acid ((S)-1-carbamoyl-3-methyl-butyl)-amide

HRID 632147Notes

Reaction equation

HRID 632147 reaction equation
C1(COC2N=C(C(O)=O)C=CC=2C2CCOC2)CC1.[CH:20]1([CH2:23][O:24][C:25]2[N:30]=[C:29]([C:31]([OH:33])=O)[CH:28]=[CH:27][C:26]=2[CH:34]2[CH2:38][CH2:37][CH2:36][O:35]2)[CH2:22][CH2:21]1.[NH2:39][C@@H:40]([CH2:44][CH:45]([CH3:47])[CH3:46])[C:41]([NH2:43])=[O:42]>>[C:41]([C@@H:40]([NH:39][C:31]([C:29]1[CH:28]=[CH:27][C:26]([CH:34]2[CH2:38][CH2:37][CH2:36][O:35]2)=[C:25]([O:24][CH2:23][CH:20]2[CH2:21][CH2:22]2)[N:30]=1)=[O:33])[CH2:44][CH:45]([CH3:47])[CH3:46])(=[O:42])[NH2:43]

Participants

4

Reactant 3

HCID 69640LeucinamideHCID 710873686-(Cyclopropylmethoxy)-5-(tetrahydrofuran-2-yl)-pyridine-2-carboxylic acidHCID 710873756-(Cyclopropylmethoxy)-5-(tetrahydrofuran-3-yl)-pyridine-2-carboxylic acid

Product 1

HCID 711056026-Cyclopropylmethoxy-5-(tetrahydro-furan-2-yl)-pyridine-2-carboxylic acid ((S)-1-carbamoyl-3-methyl-butyl)-amide

Procedure

The title compound was synthesized in analogy to Example 1, using the mixture of 6-(cyclopropylmethoxy)-5-(tetrahydrofuran-3-yl)-pyridine-2-carboxylic acid and 6-(cyclopropylmethoxy)-5-(tetrahydrofuran-2-yl)-pyridine-2-carboxylic acid (mixture from Example 114 d), and (2S)-2-amino-4-methyl-pentanamide (CAN 687-51-4) as starting materials, MS (EI): m/e=376.2 [M+H]+.

Sources & evidence

ORD record
ord-16e79be9f6014c179b6978e510987e10
Source dataset
uspto-grants-2016_04
Patent number
US09321727B2

Reaction notes

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