Pyridine → HCID 86680399, compound

HRID 1023157Notes

Reaction equation

HRID 1023157 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][C:14]=1[NH2:15])[O:5][CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8].N1C=CC=CC=1.Cl[C:23](Cl)([O:25]C(=O)OC(Cl)(Cl)Cl)Cl>C(Cl)(Cl)Cl>[O:25]=[C:23]1[NH:15][C:14]2[CH:13]=[CH:12][C:4]([O:5][CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:3][C:2]=2[NH:1]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 94429TriphosgeneHCID 57763326HCID 57763326, compound

Product 1

HCID 86680399HCID 86680399, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred solution of ethyl 2-(3,4-diaminophenoxy)acetate (144 mg, 0.685 mmol) in dry CHCl3 (5 mL) at 0° C., pyridine (0.083 mL, 1.027 mmol) and triphosgene (203 mg, 0.685 mmol) were added and allowed to stir at room temperature for two hours. Completion of the reaction was monitored by LCMS. Solvent was removed under vacuum. Water was added to the residue. The solid which formed was filtered and dried to afford crude ethyl 2-((2-oxo-2,3-dihydro-1H-benzo[d]imidazol-5-yl)oxy)acetate (85 mg, 75% by LCMS) which was used in the next step without further purification. 1H NMR: 400 MHZ, DMSO-d6: δ 1.22 (t, J=7.20 Hz, 3H), 4.18 (q, J=7.20 Hz, 2H), 4.70 (s, 2H), 6.52 (t, J=2.40 Hz, 2H), 6.81 (d, J=9.20 Hz, 1H), 10.40 (s, 1H), 10.51 (s, 1H). LCMS: RT 1.16 min. LCMS (ES-API), m/z 237.0 (M+H).

Workup

  1. customSolvent was removed under vacuum
  2. additionWater was added to the residue
  3. customThe solid which formed
  4. filtrationwas filtered
  5. customdried

Sources & evidence

ORD record
ord-459c2285bcee4c2089e8e5dcd2e4be2e
Source dataset
uspto-grants-2014_05
Patent number
US08722670B2

Reaction notes

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