Ammonium Bicarbonate → HCID 178513575, compound

HRID 2247152Notes

Reaction equation

HRID 2247152 reaction equation
[C:1]1([C:7]2([C:12]3[CH:17]=[CH:16][C:15]([C:18]4[NH:22][C:21]5[CH:23]=[CH:24][C:25]([C:27]([NH2:29])=[O:28])=[CH:26][C:20]=5[N:19]=4)=[CH:14][CH:13]=3)[O:11][CH2:10][CH2:9][O:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:30]C1C=CC(C2(C3C=CC(C4NC5C=CC(C(O)=O)=CC=5N=4)=CC=3)OCCO2)=CC=1.C(N1C=CN=C1)(N1C=CN=C1)=O.C(=O)(O)[O-].[NH4+].[NH4+].[Cl-]>CN(C=O)C>[Cl:30][C:4]1[CH:3]=[CH:2][C:1]([C:7]2([C:12]3[CH:17]=[CH:16][C:15]([C:18]4[NH:22][C:21]5[CH:23]=[CH:24][C:25]([C:27]([NH2:29])=[O:28])=[CH:26][C:20]=5[N:19]=4)=[CH:14][CH:13]=3)[O:8][CH2:9][CH2:10][O:11]2)=[CH:6][CH:5]=1

Participants

7

Reactant 5

HCID 14013Ammonium BicarbonateHCID 25517Ammonium ChlorideHCID 682631,1'-CarbonyldiimidazoleHCID 178513574HCID 178513574, compoundHCID 178524154HCID 178524154, compound

Product 1

HCID 178513575HCID 178513575, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

2-[4-(2-Phenyl-[1,3]dioxolan-2-yl)-phenyl]-1H-benzoimidazole-5-carboxylic acid amide. To a solution of 2-{4-[2-(4-chloro-phenyl)-[1,3]dioxolan-2-yl]-phenyl}-1H-benzoimidazole-5-carboxylic acid (135 mg, 0.32 mmol) in anhydrous DMF was added carbonyldiimidazole (118 mg, 0.73 mmol). The reaction mixture was stirred under N2 for 30 min and then cooled to 0° C., and ammonium bicarbonate (140 mg, 1.4 mmol) was added. The resulting mixture was allowed to warm to RT and was stirred for 16 h. The mixture was added dropwise to saturated aqueous NH4Cl. The resulting precipitate was collected by filtration and washed with H2O (100 mL) then hexanes (100 mL). The product was dried under vacuum overnight to give the title compound (1.02 mg, 76%). TLC (silica, 1% methanol saturated with ammonia/9% methanol/CH2Cl2): Rf=0.33. HPLC (Method A): Rt=7.42. MS (ESI+): mass calculated for C23H18ClN3O3, 419.1; m/z found, 420.1 [M+H]+. 1H NMR (400 MHz, CD3OD): δ 8.09 (s, 1H), 8.00 (d, J=8.4 Hz, 2H), 7.75-7.72 (dd, J=8.5, 1.5 Hz, 1H), 7.59 (d, J=8.4 Hz, 2H), 7.56 (br d, J=8.7 Hz, 1H), 7.43 (d, J=8.5 Hz, 2H), 7.27 (d, J=8.6 Hz, 2H), 3.99 (s, 4H).

Workup

  1. temperatureto warm to RT
  2. stirringwas stirred for 16 h
  3. filtrationThe resulting precipitate was collected by filtration
  4. washwashed with H2O (100 mL)
  5. customThe product was dried under vacuum overnight

Sources & evidence

ORD record
ord-c51e1f1db9984c1c865b35aaf9150f00
Source dataset
uspto-grants-2010_03
Patent number
US07687639B2

Reaction notes

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