Chloroform → HCID 4999172, compound

HRID 644285Notes

Reaction equation

HRID 644285 reaction equation
C(C1C=CC(C(N[C:12]2[CH:27]=[CH:26][CH:25]=[CH:24][C:13]=2[C:14]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][N:18]=2)=[O:15])=O)=C(OC2CCNCC2)C=1)(C)(C)C.N=C=N.C(Cl)(Cl)Cl>C(O)(C)(C)C>[Cl:23][C:20]1[CH:21]=[CH:22][C:17]([NH:16][C:14](=[O:15])[C:13]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:12]=2)=[N:18][CH:19]=1

Participants

5

Reactant 3

HCID 6212ChloroformHCID 160435CarbodiimideHCID 44434213HCID 44434213, compound

Product 1

HCID 4999172HCID 4999172, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

To 2-[4-(tert-butyl)-2-(piperidin-4-yloxy)benzoylamino]-N-(5-chloropyrdin-2-yl)benzamide (30 mg, 59 pmnol) in a 4 mL screw cap vial is added polymer-supported carbodiimide (P-EPC, 280 mg @0.85 mmol/g, 4 eq) and a carboxylic acid of choice (120 micromoles, 2 eq), followed by 3 mL of 4:1 (amylene stabilized) chloroform:tert-butyl alcohol. Where acid hydrochloride salts are used, piperidinomethyl polystyrene resin (100 mg @2.6-2.8 mmol/g) is added to effect reaction. The vial is capped, shaken overnight at room temperature, then the mixture is filtered. Retentates are washed with amylene stabilized chloroform (3 mL), and the combined filtrate and wash are concentrated in vacuo to afford the amide derivative of the compound of Example 202.

Workup

  1. customThe vial is capped
  2. filtrationthe mixture is filtered
  3. washRetentates are washed with amylene
  4. washthe combined filtrate and wash
  5. concentrationare concentrated in vacuo

Sources & evidence

ORD record
ord-59488ff879de4b5984fe7c6ea53b65e9
Source dataset
uspto-grants-2010_04
Patent number
US07700628B2

Reaction notes

Loading…