(S)-3-[(5-amino-pyridine-3-carbonyl)-amino]-tetrahydrofuran-3-carboxylic acid → (S)-5-amino-N-(3-{[3-fluoro-5-(4-methoxy-2-trifluoromethyl-phenylamino)-pyridin-2-ylmethyl]-carbamoyl}-tetrahydro-furan-3-yl)-nicotinamide

HRID 1428212Notes

Reaction equation

HRID 1428212 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]([NH:10][C@@:11]2([C:16]([OH:18])=O)[CH2:15][CH2:14][O:13][CH2:12]2)=[O:9])[CH:5]=[N:6][CH:7]=1.[NH2:19][CH2:20][C:21]1[N:26]=[CH:25][C:24]([NH:27][C:28]2[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][C:29]=2[C:36]([F:39])([F:38])[F:37])=[CH:23][C:22]=1[F:40]>>[NH2:1][C:2]1[CH:7]=[N:6][CH:5]=[C:4]([CH:3]=1)[C:8]([NH:10][C@@:11]1([C:16](=[O:18])[NH:19][CH2:20][C:21]2[C:22]([F:40])=[CH:23][C:24]([NH:27][C:28]3[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][C:29]=3[C:36]([F:39])([F:38])[F:37])=[CH:25][N:26]=2)[CH2:15][CH2:14][O:13][CH2:12]1)=[O:9]

Participants

3

Reactant 2

HCID 59496422(S)-3-[(5-amino-pyridine-3-carbonyl)-amino]-tetrahydrofuran-3-carboxylic acidHCID 66765948(6-Aminomethyl-5-fluoro-pyridin-3-yl)-(4-methoxy-2-trifluoromethyl-phenyl)-amine

Product 1

HCID 56840396(S)-5-amino-N-(3-{[3-fluoro-5-(4-methoxy-2-trifluoromethyl-phenylamino)-pyridin-2-ylmethyl]-carbamoyl}-tetrahydro-furan-3-yl)-nicotinamideYield 34%

Procedure

Analogously to Example 1e), (S)-3-[(5-amino-pyridine-3-carbonyl)-amino]-tetrahydrofuran-3-carboxylic acid (from 2b) was reacted with (6-aminomethyl-5-fluoro-pyridin-3-yl)-(4-methoxy-2-trifluoromethyl-phenyl)-amine. The product was obtained in a yield of 34% of theory.

Workup

  1. customThe product was obtained in a yield of 34% of theory

Sources & evidence

ORD record
ord-e1986ad8b8f44128a41768dfd32df69a
Source dataset
uspto-grants-2015_01
Patent number
US08937073B2

Reaction notes

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