1,2-Dichloroethane → Formate

HRID 418320

Reaction equation

HRID 418320 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:22])[NH:11][CH2:12][C:13]2[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=2)[C:16]([OH:18])=[O:17])=[CH:5][CH:4]=1)#[N:2].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1.[CH3:44][N:45]([CH3:51])[CH2:46][CH2:47][CH2:48][CH2:49][NH2:50]>CN(C=O)C>[CH:16]([O-:18])=[O:17].[C:1]([C:3]1[CH:4]=[CH:5][C:6]([NH:9][C:10](=[O:22])[NH:11][CH2:12][C:13]2[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=2)[C:16]([NH:50][CH2:49][CH2:48][CH2:47][CH2:46][N:45]([CH3:51])[CH3:44])=[O:18])=[CH:7][CH:8]=1)#[N:2]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 770634-DimethylaminobutylamineHCID 448195453-[3-(4-Cyano-phenyl)-ureidomethyl]-benzoic acid

Product 2

HCID 283FormateYield 1,599.4%HCID 250566323-[3-(4-cyano-phenyl)-ureidomethyl]-N-(4-dimethylamino-butyl)-benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-[3-(4-Cyano-phenyl)-ureidomethyl]-benzoic acid (30 mg, 0.1 mmol), prepared as described in Example 1, EDC (28.8 mg, 0.15 mmol), and HOBt (17.6 mg, 0.13 mmol) were combined in a reaction vial and DMF (1 mL) then N-methylmorpholine (0.017 mL, 0.15 mmol) were added. The reaction mixture was agitated for 30 minutes, then N1,N1-dimethyl-butane-1,4-diamine (14 mg, 0.12 mmol) was added. Shaking was continued overnight. The reaction mixture was purified by preparative HPLC using an acetonitrile/water/formic acid gradient. The title compound was collected as a formate salt (36 mg, 90% yield) following evaporation of the solvent; MS analysis electrospray, 394 (M+H).

Workup

  1. stirringShaking
  2. waitwas continued overnight
  3. customThe reaction mixture was purified by preparative HPLC

Sources & evidence

ORD record
ord-7326217a045549729ada267576f1f18a
Source dataset
uspto-grants-2012_01
Patent number
US08093266B2

Linked notes

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