Ammonia → HCID 11952314, compound

HRID 2101493Notes

Reaction equation

HRID 2101493 reaction equation
C[O:2][C:3](=O)[CH2:4][N:5]([CH2:14][C:15]1[N:16]([CH2:20][C:21]2[CH:26]=[C:25]([Cl:27])[CH:24]=[C:23]([Cl:28])[CH:22]=2)[CH:17]=[CH:18][N:19]=1)[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([F:13])[CH:8]=1.[NH3:30]>CO>[Cl:28][C:23]1[CH:22]=[C:21]([CH:26]=[C:25]([Cl:27])[CH:24]=1)[CH2:20][N:16]1[CH:17]=[CH:18][N:19]=[C:15]1[CH2:14][N:5]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([F:13])[CH:8]=1)[CH2:4][C:3]([NH2:30])=[O:2]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 11952490HCID 11952490, compound

Product 1

HCID 11952314HCID 11952314, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

[[1-(3,5-Dichloro-benzyl)-1H-imidazol-2-ylmethyl]-(3-fluoro-benzyl)-amino]-acetic acid methyl ester (7e) (81 mg, 0.19 mmol) was dissolved in a 7N solution of NH3 in MeOH (10 mL). The solution was heated at 100° C. with stirring in a sealed tube reaction vessel for 18 h. The volatiles were removed in vacuo and the residue purified by column chromatography (silica gel, 5% MeOH in CH2Cl2) to provide the desired product 7f (40 mg, 51%): ESI MS m/z 421 [C20H19Cl2FN4O+H]+.

Workup

  1. customThe volatiles were removed in vacuo
  2. customthe residue purified by column chromatography (silica gel, 5% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-c1ccda6cf75c4922bedc9c6f9ce174ee
Source dataset
uspto-grants-2009_08
Patent number
US07572921B2

Reaction notes

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