1,2-Dichloroethane → HCID 66611767, compound

HRID 2204772Notes

Reaction equation

HRID 2204772 reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[C:16]([C:18]([N:20]2[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]2)=[O:19])[C:15]([Cl:27])=[CH:14][C:10]=1[C:11]([OH:13])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[NH2:37][C:38]1[CH:39]=[N:40][CH:41]=[CH:42][CH:43]=1.ON1C2N=CC=CC=2N=N1.C(Cl)CCl>CN(C)C=O>[CH2:1]([O:8][C:9]1[CH:17]=[C:16]([C:18]([N:20]2[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]2)=[O:19])[C:15]([Cl:27])=[CH:14][C:10]=1[C:11]([NH:37][C:38]1[CH:39]=[N:40][CH:41]=[CH:42][CH:43]=1)=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 100093-AminopyridineHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 66611525HCID 66611525, compound

Product 1

HCID 66611767HCID 66611767, compoundYield 25.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(benzyloxy)-5-chloro-4-(4-methylpiperazine-1-carbonyl)benzoic acid (may be prepared as described in D 76) (108 mg, 0.278 mmol) in N,N-dimethylformamide (DMF) (5 mL) was added DIPEA (0.97 ml, 0.555 mmol), 3-aminopyridine (39.2 mg, 0.417 mmol) and 1-hydroxy-7-azabenzotriazole (HOAt) (45 mg, 0333 mmol) and EDC (96 mg, 0.5 mmol). The solution was stirred overnight. The solvent was removed in vacuo and the residue was purified by MDAP (tartan, High pH, 25 minute run) to give a white solid (33 mg, 9% yield).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by MDAP (tartan, High pH, 25 minute run)

Sources & evidence

ORD record
ord-97b5a63ef32f4e809484440281374c11
Source dataset
uspto-grants-2016_06
Patent number
US09365551B2

Reaction notes

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