Glycolic Acid → HCID 69078028, compound

HRID 225482Notes

Reaction equation

HRID 225482 reaction equation
Cl.Cl.[Cl:3][C:4]1[C:9]([F:10])=[CH:8][C:7]([C:11]2[N:12]=[C:13]([N:20]3[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]3)[C:14]3[S:19][CH:18]=[CH:17][C:15]=3[N:16]=2)=[C:6]([F:26])[CH:5]=1.[OH:27][CH2:28][C:29](O)=[O:30].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>O.CN(C=O)C.C(N(CC)CC)C>[ClH:3].[Cl:3][C:4]1[C:9]([F:10])=[CH:8][C:7]([C:11]2[N:12]=[C:13]([N:20]3[CH2:21][CH2:22][N:23]([C:28](=[O:27])[CH2:29][OH:30])[CH2:24][CH2:25]3)[C:14]3[S:19][CH:18]=[CH:17][C:15]=3[N:16]=2)=[C:6]([F:26])[CH:5]=1

Participants

8

Reactant 4

HCID 757Glycolic AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 69076795HCID 69076795, compound

Product 1

HCID 69078028HCID 69078028, compoundYield 185.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of 500 mg of 2-(4-chloro-2,5-difluorophenyl)-4-piperazine-1-ylthieno[3,2-d]pyrimidine dihydrochloride, 104 mg of hydroxyacetic acid, 0.32 ml of triethylamine, 184 mg of HOBt, 261 mg of EDCI and 10 ml of DMF was stirred for two days at room temperature. 70 ml of water was added to the reaction mixture. After the precipitate was filtered and washed with water, it was dried at 50° C. under reduced pressure. The obtained solid was dissolved in 10 ml of THF and was added to 2 ml of 4M HCl-dioxane aq. The resultant was concentrated under reduced pressure to give a solid. This solid was recrystallized from EtOH-EtOAc to give 487 mg of 2-{4-[2-(4-chloro-2,5-difluorophenyl)thieno[3,2-d]pyrimidine-4-yl]piperazine-1-yl}-2-oxoethanol hydrochloride.

Workup

  1. filtrationAfter the precipitate was filtered
  2. washwashed with water, it
  3. customwas dried at 50° C. under reduced pressure
  4. dissolutionThe obtained solid was dissolved in 10 ml of THF
  5. additionwas added to 2 ml of 4M HCl-dioxane aq. The resultant
  6. concentrationwas concentrated under reduced pressure
  7. customto give a solid
  8. customThis solid was recrystallized from EtOH-EtOAc

Sources & evidence

ORD record
ord-cc8e877e76f847e58cbea5351d93a6e2
Source dataset
uspto-grants-2009_07
Patent number
US07557112B2

Reaction notes

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