Glycolic Acid → HCID 68507661, compound

HRID 2069454Notes

Reaction equation

HRID 2069454 reaction equation
[NH2:1][CH2:2][CH:3]([OH:31])[CH2:4][O:5][C:6]1[C:11]([CH3:12])=[CH:10][C:9]([C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:23]=[C:22]([CH3:24])[N:21]=[C:20]([NH:25][CH:26]([CH3:28])[CH3:27])[N:19]=3)[N:14]=2)=[CH:8][C:7]=1[CH2:29][CH3:30].[C:32](O)(=[O:35])[CH2:33][OH:34].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>CN(C=O)C.C([O-])(O)=O.[Na+]>[CH2:29]([C:7]1[CH:8]=[C:9]([C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:23]=[C:22]([CH3:24])[N:21]=[C:20]([NH:25][CH:26]([CH3:27])[CH3:28])[N:19]=3)[N:14]=2)[CH:10]=[C:11]([CH3:12])[C:6]=1[O:5][CH2:4][C@@H:3]([OH:31])[CH2:2][NH:1][C:33](=[O:34])[CH2:32][OH:35])[CH3:30]

Participants

7

Reactant 4

HCID 757Glycolic AcidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68510920HCID 68510920, compound

Product 1

HCID 68507661HCID 68507661, compoundYield 44.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of crude 1-amino-3-{2-ethyl-4-[3-(2-isopropylamino-6-methyl-pyrimidin-4-yl)-[1,2,4]oxadiazol-5-yl]-6-methyl-phenoxy}-propan-2-ol (43 mg, 97 μmol) in DMF, glycolic acid (11 mg, 146 μmol), HOBt (20 mg, 146 μmol), and EDC hydrochloride (28 mg, 146 μmol) are added. The mixture is stirred at rt for 18 h before it is diluted with sat. aq. NaHCO3 and extracted twice with EtOAc. The combined org. extracts are dried over MgSO4, filtered and concentrated. The crude product is purified by prep. TLC plates with DCM containing 10% of 7M NH3 in MeOH to give (S)—N-(3-{2-ethyl-4-[3-(2-isopropylamino-6-methyl-pyrimidin-4-yl)-[1,2,4]oxadiazol-5-yl]-6-methyl-phenoxy}-2-hydroxy-propyl)-2-hydroxy-acetamide (21 mg) as a white solid; LC-MS: tR=0.85 min; [M+H]+=485.14; 1H NMR (CDCl3): δ 1.29 (m, 9H), 2.35 (m, 3H), 2.46 (s, 3H), 2.72 (q, J=7.5 Hz, 2H), 3.52 (m, 1H), 3.76 (m, 1H), 3.87 (m, 3H), 4.20 (m, 3H), 4.31 (m, 1H), 5.31 (m, 1H), 7.22 (s, 1H), 7.25 (t, J=6.0 Hz, 1H), 7.89 (s, 1H), 7.91 (s, 1H).

Workup

  1. extractionextracted twice with EtOAc
  2. dry with materialextracts are dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product is purified by prep

Sources & evidence

ORD record
ord-0d729f3012414bafad34c235f5848422
Source dataset
uspto-grants-2012_10
Patent number
US08299086B2

Reaction notes

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