1,2-Dichloroethane → HCID 178475145, compound

HRID 705886Notes

Reaction equation

HRID 705886 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][O:17][C:18]3[NH:19][CH:20]=[C:21]([CH2:25][C:26]([OH:28])=O)[C:22](=[O:24])[N:23]=3)=[CH:11][CH:10]=2)=[CH:4][C:3]=1[C:29]([F:32])([F:31])[F:30].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[C:47]([NH:50][NH2:51])(=[O:49])[CH3:48]>C1COCC1>[C:47]([NH:50][NH:51][C:26](=[O:28])[CH2:25][C:21]1[C:22](=[O:24])[N:23]=[C:18]([O:17][CH2:16][CH2:15][C:12]2[CH:13]=[CH:14][C:9]([O:8][C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([C:29]([F:30])([F:32])[F:31])[CH:4]=3)=[CH:10][CH:11]=2)[NH:19][CH:20]=1)(=[O:49])[CH3:48]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 14039AcetohydrazideHCID 757711-HydroxybenzotriazoleHCID 178525227HCID 178525227, compound

Product 1

HCID 178475145HCID 178475145, compoundYield 27.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2-{[2-(4-{[4-chloro-3-(trifluoromethyl)phenyl]oxy}phenyl)ethyl]oxy}-4-oxo-1,4-dihydro-5-pyrimidinyl)acetic acid (91 mg, 0.194 mmol) in THF (2 mL) was added EDC (149 mg, 0.776 mmol) and HOBT (89 mg, 0.582 mmol). The mixture was stirred at room temperature for 15 min and acetohydrazide (21.57 mg, 0.291 mmol) was added. The mixture was stirred at room temperature overnight. Purification via reverse phase flash chromatography then afforded the title compound (28 mg, 0.053 mmol, 27.5% yield). LCMS: rt=3.04 min, [M+H+]=525

Workup

  1. stirringThe mixture was stirred at room temperature overnight
  2. customPurification via reverse phase flash chromatography

Sources & evidence

ORD record
ord-7c8ca09434264d4eaee4e5166ac36375
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

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