1,2-Dichloroethane → HCID 67107263, compound

HRID 1623763Notes

Reaction equation

HRID 1623763 reaction equation
C(N(CC)CC)C.[N:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH2:14].[Br:15][C:16]1[CH:17]=[CH:18][C:19]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[C:20]([CH:24]=1)[C:21](O)=[O:22].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.O>[Br:15][C:16]1[CH:17]=[CH:18][C:19]([O:25][CH2:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)=[C:20]([CH:24]=1)[C:21]([NH:14][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][N:8]=1)=[O:22]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 104392-AminopyridineHCID 757711-HydroxybenzotriazoleHCID 24613572-(Benzyloxy)-5-bromobenzoic acid

Product 1

HCID 67107263HCID 67107263, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

Neat triethylamine (0.27 ml, 1.95 mmol) and pyridin-2-amine (61.3 mg, 0.65 mmol) were added to a stirred suspension of 5-bromo-2-[(phenylmethyl)oxy]benzoic acid (may be prepared as described in Description 5, method C; 200 mg, 0.65 mmol), EDC (250 mg, 1.30 mmol) and HOBT (199 mg, 1.30 mmol) in DMF (3 ml) at 20° C. The reaction mixture was stirred at 20° C. overnight and was then poured into 15 ml water and filtered. The residue was washed with methanol (10 ml) to yield the title compound. The mother liquid was evaporated and the solid was purified by preparative HPLC, (A: 10 mmol ammonium carbonate/water B: acetonitrile) to yield the title compound. The two batches of product were mixed. 47 mg.

Workup

  1. filtrationfiltered
  2. washThe residue was washed with methanol (10 ml)

Sources & evidence

ORD record
ord-1531835ca8ff40ec877722df6c99bd9d
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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