1,2-Dichloroethane → N-(2-Aminophenyl)-4-((3-(6-methoxypyridin-3-yl)-1H-pyrazol-5-ylamino)methyl)benzamide

HRID 416302Notes

Reaction equation

HRID 416302 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([C:9]2[CH:13]=[C:12]([NH:14][CH2:15][C:16]3[CH:24]=[CH:23][C:19]([C:20]([OH:22])=O)=[CH:18][CH:17]=3)[NH:11][N:10]=2)=[CH:5][CH:4]=1.CCN(CC)CC.C(Cl)CCl.[CH:36]1[CH:37]=[CH:38][C:39]2[N:44](O)N=[N:42][C:40]=2[CH:41]=1.C1(N)C=CC=CC=1N>CC#N>[NH2:42][C:40]1[CH:41]=[CH:36][CH:37]=[CH:38][C:39]=1[NH:44][C:20](=[O:22])[C:19]1[CH:18]=[CH:17][C:16]([CH2:15][NH:14][C:12]2[NH:11][N:10]=[C:9]([C:6]3[CH:7]=[N:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[CH:13]=2)=[CH:24][CH:23]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 7243O-PhenylenediamineHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 178488659HCID 178488659, compound

Product 1

HCID 178488658N-(2-Aminophenyl)-4-((3-(6-methoxypyridin-3-yl)-1H-pyrazol-5-ylamino)methyl)benzamideYield 14%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 385 (640 mg, 1.97 mmol) in MeCN (10 mL) was sequentially treated with Et3N (831 μL, 603 mg, 5.96 mmol), EDC (571 mg, 2.98 mmol), HOBT (334 mg, 2.18 mmol) and 1,2-phenylene diamine (429 mg, 3.97 mmol) and allowed to stir overnight. The reaction mixture was concentrated and partitioned between DCM (15 mL) and saturated NH4Cl (15 mL). The organic phase was collected, dried with Na2SO4, filtered and concentrated. The resultant solid was purified by flash chromatography using the gradient 3-15% MeOH in DCM to afford the title compound (113 mg, 14% yield). 1H NMR (DMSO-d6) 9.65 (s, 1H), 8.43 (s, 1H), 7.92 (m, 3H), 7.48 (d, J=8.0 Hz, 2H), 7.16 (d, J=7.4 Hz, 1H), 6.97 (t, J=7.6 Hz, 1H), 6.81 (t, J=8.2 Hz, 2H), 6.63 (t, J=7.4 Hz, 1H), 5.85 (s, 1H), 4.34 (s, 2H), 3.85 (s, 3H). LRMS: (calc) 414.2; (found) 415.3 (M+H1)

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompartitioned between DCM (15 mL) and saturated NH4Cl (15 mL)
  3. customThe organic phase was collected
  4. dry with materialdried with Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resultant solid was purified by flash chromatography

Sources & evidence

ORD record
ord-305c43248ca542b9a9b9dc8061a4c219
Source dataset
uspto-grants-2012_01
Patent number
US08088805B2

Reaction notes

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