1,1'-Carbonyldiimidazole → HCID 135492557, compound

HRID 1790282Notes

Reaction equation

HRID 1790282 reaction equation
CO[C:3](=[O:17])[C:4]1[CH:9]=[C:8]([N:10]2[C:14](=[O:15])[NH:13][CH:12]=[N:11]2)[CH:7]=[CH:6][C:5]=1[Cl:16].Cl.[NH2:19][CH2:20][C:21]1([OH:28])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1.C1N=CN(C(N2C=NC=C2)=O)C=1.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.CN(C1C=CN=CC=1)C>[Cl:16][C:5]1[CH:6]=[CH:7][C:8]([N:10]2[C:14](=[O:15])[NH:13][CH:12]=[N:11]2)=[CH:9][C:4]=1[C:3]([NH:19][CH2:20][C:21]1([OH:28])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1)=[O:17]

Participants

7

Reactant 4

HCID 682631,1'-CarbonyldiimidazoleHCID 757711-HydroxybenzotriazoleHCID 184386471-(Aminomethyl)cycloheptanol hydrochlorideHCID 136344287HCID 136344287, compound

Product 1

HCID 135492557HCID 135492557, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To 2-chloro-5-(5-oxo-4,5-dihydro-[1,2,4]triazol-1-yl)-benzoic acid methyl ester (48.0 mg, 0.2 mmol) in DMF (3 mL) was added 1-aminomethyl-cycloheptanol HCl (54.0 mg, 0.3 mmol), polymer-supported CDI (660 mg, 0.6 mmol), polymer-supported DMAP (280 mg, 0.20 mmol), and HOBt (40.0 mg, 0.3 mmol). The resulting reaction was shaken for 3 hours at ambient temperature. The reaction was filtered, washed with methanol, and the filtrate concentrated in vacuo. The residue was purified by reverse phase HPLC using a (5–100% gradient of 0.1% formic acid in acetonitrile and 0.1% formic acid in water) to yield 20 mg of the above named compound.

Workup

  1. customThe resulting reaction
  2. filtrationThe reaction was filtered
  3. washwashed with methanol
  4. concentrationthe filtrate concentrated in vacuo
  5. customThe residue was purified by reverse phase HPLC
  6. customto yield 20 mg of the

Sources & evidence

ORD record
ord-65a98d94232b4a8dbc1370dbf320c0ca
Source dataset
uspto-grants-2006_07
Patent number
US07071223B1

Reaction notes

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