Trifluoroacetic acid → HCID 11951062, compound

HRID 1984078Notes

Reaction equation

HRID 1984078 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-ylmethyl)-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 concetration affroded 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. dry with materialdrying (Na2SO4) and concetration

Sources & evidence

ORD record
ord-9809635cc2d041669e58ad16739e8f3e
Source dataset
uspto-grants-2009_06
Patent number
US07544672B2

Reaction notes

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