1,2-Dichloroethane → HCID 86694932, compound

HRID 2204752Notes

Reaction equation

HRID 2204752 reaction equation
[Br:1][C:2]1[C:10]([CH2:11][N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[CH:9][C:5]([C:6]([OH:8])=O)=[C:4]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:3]=1.C(N(C(C)C)CC)(C)C.[CH:35]1[CH:36]=C[C:38]2[N:43](O)N=[N:41][C:39]=2[CH:40]=1.NC1C=NC=CC=1.C(Cl)CCl>CN(C)C=O>[Br:1][C:2]1[C:10]([CH2:11][N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[CH:9][C:5]([C:6]([NH:41][C:39]2[CH:38]=[N:43][CH:36]=[CH:35][CH:40]=2)=[O:8])=[C:4]([O:18][CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:3]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 100093-AminopyridineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 66611351HCID 66611351, compound

Product 1

HCID 86694932HCID 86694932, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension of 4-bromo-5-(4-morpholinylmethyl)-2-[(phenylmethyl)oxy]benzoic acid (may be prepared as described in Description 35; 100 mg, 0.25 mmol) in N,N-dimethylformamide (5 ml) was added diisopropylethylamine (0.09 ml, 0.49 mmol), HOBT (45.2 mg, 0.30 mmol), 3-aminopyridine (30.1 mg, 0.32 mmol) and EDC (94 mg, 0.49 mmol). The mixture was heated at 50° C. for 5 hours to allow dissolution. The solvent was removed in vacuo and purified by MDAP to yield the title compound as a white solid. 67 mg.

Workup

  1. dissolutiondissolution
  2. customThe solvent was removed in vacuo
  3. custompurified by MDAP

Sources & evidence

ORD record
ord-47598c83080d482b8f8423c3ddda6aea
Source dataset
uspto-grants-2016_06
Patent number
US09365551B2

Reaction notes

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