Glycolic Acid → HCID 67265520, compound

HRID 1685765Notes

Reaction equation

HRID 1685765 reaction equation
[C:1]([OH:5])(=O)[CH2:2][OH:3].CCN(C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[CH2:37]([N:39]([CH2:42][C:43]1[S:47][C:46]([C:48]2[O:52][N:51]=[C:50]([C:53]3[CH:58]=[CH:57][C:56]([CH2:59][CH2:60][NH2:61])=[CH:55][CH:54]=3)[N:49]=2)=[CH:45][C:44]=1[CH3:62])[CH2:40][CH3:41])[CH3:38]>CN(C=O)C>[CH2:37]([N:39]([CH2:42][C:43]1[S:47][C:46]([C:48]2[O:52][N:51]=[C:50]([C:53]3[CH:54]=[CH:55][C:56]([CH2:59][CH2:60][NH:61][C:1](=[O:5])[CH2:2][OH:3])=[CH:57][CH:58]=3)[N:49]=2)=[CH:45][C:44]=1[CH3:62])[CH2:40][CH3:41])[CH3:38]

Participants

7

Reactant 5

HCID 757Glycolic AcidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 67265437HCID 67265437, compound

Product 1

HCID 67265520HCID 67265520, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of glycolic acid (15 mg, 202 μmol) and DIPEA (35 mg, 270 μmol) in DMF (5 mL) is added HOBt (27 mg, 202 μmol) and EDC hydrochloride (39 mg, 202 μmol) at 0° C. The mixture is stirred for 15 min at 0° C. Then 2-{4-[5-(5-diethylaminomethyl-4-methyl-thiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-phenyl}-ethylamine is added and stirring is continued for 1 h at 0° C. The reaction is quenched with water, diluted with sat. aq. NaHCO3 and the mixture is extracted three times with EA. The combined organic extracts are dried over MgSO4, filtered and concentrated. The crude product is purified on prep. TLC plates using DCM containing 10% of 7 N NH3 in methanol to give the title compound (4 mg) as a colourless oil; LC-MS: tR=0.69 min; [M+1]+=429.06.

Workup

  1. stirringstirring
  2. waitis continued for 1 h at 0° C
  3. customThe reaction is quenched with water
  4. additiondiluted with sat. aq. NaHCO3
  5. extractionthe mixture is extracted three times with EA
  6. dry with materialThe combined organic extracts are dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product is purified on prep

Sources & evidence

ORD record
ord-e733ef2d545a41968c2e145ece6a88eb
Source dataset
uspto-grants-2012_04
Patent number
US08148410B2

Reaction notes

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