1,2-Dichloroethane → HCID 68690135, compound

HRID 2354079Notes

Reaction equation

HRID 2354079 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([NH:8][C:9](=[O:15])[NH:10][CH2:11][C:12]([OH:14])=O)[CH:5]=[CH:4][N:3]=1.[CH2:16]([CH:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH2:16]([CH:23]1[CH2:28][CH2:27][N:26]([C:12](=[O:14])[CH2:11][NH:10][C:9]([NH:8][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([CH3:1])[CH:7]=2)=[O:15])[CH2:25][CH2:24]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 317384-BenzylpiperidineHCID 757711-HydroxybenzotriazoleHCID 58816583HCID 58816583, compound

Product 1

HCID 68690135HCID 68690135, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a cooled (0° C.) mixture of [3-(2-methyl-pyridin-4-yl)-ureido]-acetic acid (Example D3., 105 mg, 0.5 mmol), 4-benzylpiperidine (Example A1., 105 mg, 0.6 mmol), HOBt (81 mg, 0.6 mmol), TEA (0.14 mL, 1 mmol) and a cat. amount of DMAP in CH2Cl2 (20 mL) are added, followed by EDC (115 mg, 0.6 mmol). The mixture is stirred at r.t. for 15 h. The mixture is quenched with sat. aq. Na2CO3 (25 mL), the phases are separated, and the aq. phase is extracted with CH2Cl2 (3×30 mL). The combined organic extracts are dried (Na2SO4), filtered and evaporated to provide the crude title compound.

Workup

  1. temperatureTo a cooled
  2. customThe mixture is quenched with sat. aq. Na2CO3 (25 mL)
  3. customthe phases are separated
  4. extractionthe aq. phase is extracted with CH2Cl2 (3×30 mL)
  5. dry with materialThe combined organic extracts are dried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-cf322c6b041e4558adf711d9f51f1a9e
Source dataset
uspto-grants-2010_07
Patent number
US07750161B2

Reaction notes

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