2,5-Pyridinediamine → N'-(6-aminopyridin-3-yl)-N-(2-cyclopentylethyl)-4-methyl-benzene-1,3-dicarboxamide

HRID 453384Notes

Reaction equation

HRID 453384 reaction equation
[CH:1]1([CH2:6][CH2:7][NH:8][C:9]([C:11]2[CH:12]=[CH:13][C:14]([CH3:20])=[C:15]([CH:19]=2)[C:16]([OH:18])=O)=[O:10])[CH2:5][CH2:4][CH2:3][CH2:2]1.CCN(C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1.Cl.CN(C)CCCN=C=NCC.[NH2:52][C:53]1[CH:58]=[CH:57][C:56]([NH2:59])=[CH:55][N:54]=1>C(Cl)Cl>[NH2:52][C:53]1[N:54]=[CH:55][C:56]([NH:59][C:16](=[O:18])[C:15]2[CH:19]=[C:11]([CH:12]=[CH:13][C:14]=2[CH3:20])[C:9]([NH:8][CH2:7][CH2:6][CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5]2)=[O:10])=[CH:57][CH:58]=1

Participants

7

Reactant 5

HCID 203142,5-PyridinediamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 593819165-((2-Cyclopentylethyl)carbamoyl)-2-methylbenzoic acid

Product 1

HCID 24812718N'-(6-aminopyridin-3-yl)-N-(2-cyclopentylethyl)-4-methyl-benzene-1,3-dicarboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a RBF was charged 5-((2-cyclopentylethyl)carbamoyl)-2-methylbenzoic acid (0.25 g, 0.91 mmol), DCM (3 ml), n,n-diisopropylethylamine (0.6 ml, 3.5 mmol), HOBt (0.14 g, 1.0 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.21 g, 1.1 mmol), and 2,5-diaminopyridine (0.1 g, 0.91 mmol) in that order. This mixture was stirred at RT under N2 for 18 h. The reaction was partitioned between DCM (30 ml) and brine (20 mL). The precipitate formed was collected, washed with water, dried in a vacuum oven overnight to give N3-(6-aminopyridin-3-yl)-N1-(2-cyclopentylethyl)-4-methylisophthalamide as a purple solid. MS (ESI, pos. ion) m/z: 367.2 (M+1).

Workup

  1. customThe reaction was partitioned between DCM (30 ml) and brine (20 mL)
  2. customThe precipitate formed
  3. customwas collected
  4. washwashed with water
  5. customdried in a vacuum oven overnight

Sources & evidence

ORD record
ord-99c5a2ef468c477490b14a80e1762d93
Source dataset
uspto-grants-2013_07
Patent number
US08492404B2

Reaction notes

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