Trifluoroacetic acid → HCID 11951062, compound

HRID 417851Notes

Reaction equation

HRID 417851 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][CH2:10][C:11]#[C:12][C:13]1[C:21]2[C:20]([Cl:22])=[N:19][C:18]([NH2:23])=[N:17][C:16]=2[N:15]([CH2:24][C:25]2[C:30]([CH3:31])=[C:29]([O:32][CH3:33])[C:28]([CH3:34])=[CH:27][N:26]=2)[CH:14]=1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:7][CH2:8][CH2:9][CH2:10][C:11]#[C:12][C:13]1[C:21]2[C:20]([Cl:22])=[N:19][C:18]([NH2:23])=[N:17][C:16]=2[N:15]([CH2:24][C:25]2[C:30]([CH3:31])=[C:29]([O:32][CH3:33])[C:28]([CH3:34])=[CH:27][N:26]=2)[CH:14]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57713839HCID 57713839, compound

Product 1

HCID 11951062HCID 11951062, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of {5-[2-amino-4-chloro-7-(4-methoxy-3,5-dimethyl-pyridin-2-ylmethy)-7H-pyrrolo [2,3-d]pyrimidin-5-yl]-pent-4-ynyl}-carbamic acid tert-butyl ester (see previous example, 33 mg) in DCM (1.0 mL) was treated with TFA (0.2 mL) at rt for 10 min. The reaction mixture was concentrated, taken in water (1.5 mL), washed with EtOAc (1.5 mL), made alkaline with sat. aq. NH4OH (0.5 mL), and back-extracted into EtOAc (25 mL). Washing (NH4OH 1M), drying (Na2SO4) and concentration afforded the title compound. tR=4.37 min. 1H NMR (CDCl3) δ 8.15 (s, 1H), 6.97 (s, 1H), 5.25 (s, 2H), 3.72 (s, 3H), 2.94 (m, 2H), 2.48 (t, 2H), 2.23 (s, 3H), 2.16 (s, 3H), 1.80 (quint., 2H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. washwashed with EtOAc (1.5 mL)
  3. extractionback-extracted into EtOAc (25 mL)
  4. washWashing (NH4OH 1M)
  5. customdrying
  6. concentration(Na2SO4) and concentration

Sources & evidence

ORD record
ord-73d390c4e1324843b6e0254d007bffd0
Source dataset
uspto-grants-2012_01
Patent number
US08093229B2

Reaction notes

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