1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 86615855, compound

HRID 225483Notes

Reaction equation

HRID 225483 reaction equation
[ClH:1].[Cl:2][C:3]1[C:8]([F:9])=[CH:7][C:6]([C:10]2[N:11]=[C:12]([N:19]3[CH2:24][CH2:23][CH:22]([CH2:25][C:26]([OH:28])=O)[CH2:21][CH2:20]3)[C:13]3[S:18][CH:17]=[CH:16][C:14]=3[N:15]=2)=[C:5]([F:29])[CH:4]=1.[Cl-].[NH4+:31].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>O.CN(C=O)C.C(N(CC)CC)C>[Cl:2][C:3]1[C:8]([F:9])=[CH:7][C:6]([C:10]2[N:11]=[C:12]([N:19]3[CH2:24][CH2:23][CH:22]([CH2:25][C:26]([NH:31][Cl:1])=[O:28])[CH2:21][CH2:20]3)[C:13]3[S:18][CH:17]=[CH:16][C:14]=3[N:15]=2)=[C:5]([F:29])[CH:4]=1

Participants

8

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 69076175HCID 69076175, compound

Product 1

HCID 86615855HCID 86615855, compoundYield 115.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of 500 mg of {1-[2-(4-chloro-2,5-difluorophenyl)thieno[3,2-d]pyrimidine-4-yl]piperidine-4-yl}acetic acid hydrochloride, 316 mg of ammonium chloride, 0.82 ml of triethylamine, 319 mg of HOBt, 452 mg of EDCI and 10 ml of DMF was stirred for 5 days at room temperature. 60 ml of water was added to the reaction mixture and 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 solution. The resultant was concentrated under reduced pressure to give a solid. This solid washed with ether to give 573 mg of 2-{1-[2-(4-chloro-2,5-difluorophenyl)thieno[3,2-d]pyrimidine-4-yl]piperidine-4-yl}acetamido 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 solution
  6. concentrationThe resultant was concentrated under reduced pressure
  7. customto give a solid
  8. washThis solid washed with ether

Sources & evidence

ORD record
ord-d88d812a787b4978a269ae3518682a61
Source dataset
uspto-grants-2009_07
Patent number
US07557112B2

Reaction notes

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