(S)-3-[(5-amino-pyridine-3-carbonyl)-amino]-tetrahydrofuran-3-carboxylic acid → (S)-5-amino-N-{3-[4-(4-methoxy-2-trifluoromethyl-phenylamino)-benzylcarbamoyl]-tetrahydrofuran-3-yl}-nicotinamide

HRID 1428215Notes

Reaction equation

HRID 1428215 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[CH: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][CH:22]=1>>[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[CH:22]=[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:37])([F:38])[F:39])=[CH:25][CH: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 66765571(4-Aminomethyl-phenyl)-(4-methoxy-2-trifluoromethyl-phenyl)-amine

Product 1

HCID 56649698(S)-5-amino-N-{3-[4-(4-methoxy-2-trifluoromethyl-phenylamino)-benzylcarbamoyl]-tetrahydrofuran-3-yl}-nicotinamideYield 32%

Procedure

Analogously to Example 1e), (S)-3-[(5-amino-pyridine-3-carbonyl)-amino]-tetrahydrofuran-3-carboxylic acid (1.00 mmol) was reacted with (4-aminomethyl-phenyl)-(4-methoxy-2-trifluoromethyl-phenyl)-amine (1.00 mMol, from Example 4b)). The product was obtained in a yield of 32% of theory.

Workup

  1. customThe product was obtained in a yield of 32% of theory

Sources & evidence

ORD record
ord-afb47b74448e4b14a844c76581ba5df0
Source dataset
uspto-grants-2015_01
Patent number
US08937073B2

Reaction notes

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