Diisopropylethylamine → HCID 59021525, compound

HRID 2219948Notes

Reaction equation

HRID 2219948 reaction equation
C([N:8]1[CH2:17][CH2:16][C:15]2[C:14]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([S:25]([C:28]([F:31])([F:30])[F:29])(=[O:27])=[O:26])=[CH:21][CH:20]=3)=[N:13][CH:12]=[N:11][C:10]=2[CH2:9]1)C1C=CC=CC=1.ClC(OC(Cl)=O)C.C(N(CC)C(C)C)(C)C>C(Cl)(Cl)Cl>[F:31][C:28]([F:29])([F:30])[S:25]([C:22]1[CH:23]=[CH:24][C:19]([NH:18][C:14]2[C:15]3[CH2:16][CH2:17][NH:8][CH2:9][C:10]=3[N:11]=[CH:12][N:13]=2)=[CH:20][CH:21]=1)(=[O:26])=[O:27]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 5213051-Chloroethyl chloroformateHCID 59021521HCID 59021521, compound

Product 1

HCID 59021525HCID 59021525, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

7-Benzyl-5,6,7,8-tetrahydro-N-(4-(trifluoromethylsulfonyl)phenyl)pyrido[3,4-d]pyrimidin-4-amine (270 mg, 0.55 mmol) was dissolved in anhydrous chloroform (10 mL) and 1-chloroethylchloroformate was added (0.18 mL, 1.65 mmol). After stirring for 30 min, N,N-diisopropylethylamine was added (0.24 mL, 1.65 mmol) and the mixture was stirred for an additional 2 h. The chloroform was removed under vacuum and 30 ml of methanol was added and the mixture was heated for 30 min. Upon reaction completion, the methanol was removed and the residue was dissolved in ethyl acetate and washed with sat. NaHCO3 and brine. The organic layer was dried over Na2SO4, filtered and evaporated to give the product (163 mg, 83%). The crude material was used for the next step.

Workup

  1. stirringthe mixture was stirred for an additional 2 h
  2. customThe chloroform was removed under vacuum and 30 ml of methanol
  3. additionwas added
  4. temperaturethe mixture was heated for 30 min
  5. customUpon reaction completion
  6. customthe methanol was removed
  7. dissolutionthe residue was dissolved in ethyl acetate
  8. washwashed with sat. NaHCO3 and brine
  9. dry with materialThe organic layer was dried over Na2SO4
  10. filtrationfiltered
  11. customevaporated

Sources & evidence

ORD record
ord-45680bc7ef9a4422849fc67ee1adb31b
Source dataset
uspto-grants-2008_08
Patent number
US07414131B2

Reaction notes

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