Dichloromethane → N3-(6-aminopyridin-3-yl)-N1-(cyclopropylmethyl)-4-methylisophthalamide

HRID 2355108Notes

Reaction equation

HRID 2355108 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[CH:12]=[C:13]([CH:17]=[CH:18][C:19]=2[CH3:20])[C:14]([OH:16])=O)=[O:10])=[CH:4][CH:3]=1.C(Cl)Cl.Cl.CN(C)CCCN=C=NCC.[NH2:36][CH2:37][CH:38]1[CH2:40][CH2:39]1>CN(C=O)C>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([NH:8][C:9](=[O:10])[C:11]2[CH:12]=[C:13]([CH:17]=[CH:18][C:19]=2[CH3:20])[C:14]([NH:36][CH2:37][CH:38]2[CH2:40][CH2:39]2)=[O:16])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 75646CyclopropanemethanamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 593818933-((6-Aminopyridin-3-yl)carbamoyl)-4-methylbenzoic acid

Product 1

HCID 59381908N3-(6-aminopyridin-3-yl)-N1-(cyclopropylmethyl)-4-methylisophthalamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a round-bottomed flask was charged 3-((6-aminopyridin-3-yl)carbamoyl)-4-methylbenzoic acid (70 mg, 0.26 mmol), DCM (1 ml), and DMF (1 ml). 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (74 mg, 0.39 mmol) was then added. The reaction mixture was stirred for 10 min before (aminomethyl)cyclopropane (27 μl, 0.31 mmol) was introduced. The reaction mixture was stirred at RT under N2 for 16 h. The reaction was partitioned between DCM (15 ml) and brine (10 mL). The aqueous layer was back exacted with DCM (3×10 mL) and the combined DCM layer was dried (Na2SO4) and concentrated. The crude product was dissolved in DCM and purified by chromatography through a Redi-Sep® pre-packed silica gel column (40 g), eluting with a gradient of 0% to 10% MeOH in CH2Cl2, to provide N3-(6-aminopyridin-3-yl)-N1-(cyclopropylmethyl)-4-methylisophthalamide as an off-white solid. m/z: 325.2 (M+1).

Workup

  1. additionwas introduced
  2. customThe reaction was partitioned between DCM (15 ml) and brine (10 mL)
  3. dry with materialthe combined DCM layer was dried (Na2SO4)
  4. concentrationconcentrated
  5. dissolutionThe crude product was dissolved in DCM
  6. custompurified by chromatography through a Redi-Sep® pre-packed silica gel column (40 g)
  7. washeluting with a gradient of 0% to 10% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-fb3a3830df5b48f9ae7e00f4f80480c2
Source dataset
uspto-grants-2010_07
Patent number
US07754717B2

Reaction notes

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