Trifluoroacetic acid → HCID 59333629, compound

HRID 1876524Notes

Reaction equation

HRID 1876524 reaction equation
C(OC([N:8](C(OC(C)(C)C)=O)[C:9]1[N:14]=[CH:13][C:12]([C:15]2[N:23]=[C:22]3[C:18]([N:19]=[C:20]([Cl:36])[N:21]3[C@H:24]3[CH2:28][CH2:27][N:26](C(OC(C)(C)C)=O)[CH2:25]3)=[C:17]([N:37]3[CH2:42][CH2:41][O:40][CH2:39][CH2:38]3)[N:16]=2)=[CH:11][N:10]=1)=O)(C)(C)C.FC(F)(F)C(O)=O.C(N(CC)CC)C.[CH3:64][S:65](Cl)(=[O:67])=[O:66]>C(Cl)Cl>[Cl:36][C:20]1[N:21]([C@H:24]2[CH2:28][CH2:27][N:26]([S:65]([CH3:64])(=[O:67])=[O:66])[CH2:25]2)[C:22]2[C:18]([N:19]=1)=[C:17]([N:37]1[CH2:42][CH2:41][O:40][CH2:39][CH2:38]1)[N:16]=[C:15]([C:12]1[CH:13]=[N:14][C:9]([NH2:8])=[N:10][CH:11]=1)[N:23]=2

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 59333509HCID 59333509, compound

Product 1

HCID 59333629HCID 59333629, compoundYield 42.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl (3S)-3-(2-{2-[bis(tert-butoxycarbonyl)amino]pyrimidin-5-yl}-8-chloro-6-morpholin-4-yl-9H-purin-9-yl)pyrrolidine-1-carboxylate (1.32 g, 1.88 mmol) was dissolved in methylene chloride (5 ml) followed by the addition of trifluoroacetic acid (5 ml) and the resulting mixture was stirred for 0.5 hours. The solvent was removed azeotropically with toluene and evaporated under reduced pressure. The residue was dissolved in methylene chloride followed by the addition of triethylamine (1 ml) and methanesulfonyl chloride (170 μl, 2.26 mmol) with ice cooling and the resulting mixture was stirred at room temperature for 4 hours. The reaction mixture was partitioned with ethyl acetate and water, and the solid that was not dissolved in either layer was collected by filtration, washed with ethyl acetate and water, and dried. This solid was suspended in methylene chloride, and then the insoluble matter was collected by filtration and dried to give the title compound (0.38 g, 42%) as a pale grey solid.

Workup

  1. customThe solvent was removed azeotropically with toluene
  2. customevaporated under reduced pressure
  3. dissolutionThe residue was dissolved in methylene chloride
  4. stirringthe resulting mixture was stirred at room temperature for 4 hours
  5. customThe reaction mixture was partitioned with ethyl acetate and water
  6. dissolutionthe solid that was not dissolved in either layer
  7. filtrationwas collected by filtration
  8. washwashed with ethyl acetate and water
  9. customdried
  10. filtrationthe insoluble matter was collected by filtration
  11. customdried

Sources & evidence

ORD record
ord-43a1137a0d7244a9809d78e963441e43
Source dataset
uspto-grants-2012_11
Patent number
US08309546B2

Reaction notes

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