Glycolic Acid → HCID 118023732, compound

HRID 2171818Notes

Reaction equation

HRID 2171818 reaction equation
[CH3:1][C:2]1([CH3:27])[CH2:7][CH2:6][CH:5]([C:8]2[S:26][C:11]3[N:12]=[C:13]([CH3:25])[N:14]=[C:15]([CH2:16][N:17]4[CH2:22][CH2:21][NH:20][CH2:19][C:18]4([CH3:24])[CH3:23])[C:10]=3[CH:9]=2)[CH2:4][CH2:3]1.[C:28](O)(=[O:31])[CH2:29][OH:30].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[NH4+].[Cl-]>CN1C(=O)CCC1>[CH3:1][C:2]1([CH3:27])[CH2:7][CH2:6][CH:5]([C:8]2[S:26][C:11]3[N:12]=[C:13]([CH3:25])[N:14]=[C:15]([CH2:16][N:17]4[CH2:22][CH2:21][N:20]([C:29](=[O:30])[CH2:28][OH:31])[CH2:19][C:18]4([CH3:23])[CH3:24])[C:10]=3[CH:9]=2)[CH2:4][CH2:3]1

Participants

7

Reactant 5

HCID 757Glycolic AcidHCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 118024061HCID 118024061, compound

Product 1

HCID 118023732HCID 118023732, compoundYield 39.9%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a mixture of 6-(4,4-dimethylcyclohexyl)-4-[(2,2-dimethylpiperazin-1-yl)methyl]-2-methylthieno[2,3-d]pyrimidine (222 mg), glycolic acid (52 mg), and NMP (3.2 mL) were added HATU (306 mg) and DIPEA (492 μL), followed by stirring at room temperature overnight. To the reaction mixture was added a saturated aqueous NH4Cl solution, followed by extraction with EtOAc. The organic layer was washed sequentially with water and brine, dried over MgSO4, and then concentrated under reduced pressure. The residue was purified by silica gel column to obtain 1-(4-{[6-(4,4-dimethylcyclohexyl)-2-methylthieno[2,3-d]pyrimidin-4-yl]methyl}-3,3-dimethylpiperazin-1-yl)-2-hydroxyethanone (102 mg).

Workup

  1. extractionfollowed by extraction with EtOAc
  2. washThe organic layer was washed sequentially with water and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column

Sources & evidence

ORD record
ord-9ecbd8f549b14c4fabb28a63c80618ac
Source dataset
uspto-grants-2015_06
Patent number
US09051339B2

Reaction notes

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