Trifluoroacetic acid → HCID 57713851, compound

HRID 417849Notes

Reaction equation

HRID 417849 reaction equation
C(OC(=O)[NH:7][CH2:8][C:9]#[C:10][C:11]1[C:19]2[C:18]([Cl:20])=[N:17][C:16]([NH2:21])=[N:15][C:14]=2[N:13]([CH2:22][C:23]2[C:28]([CH3:29])=[C:27]([O:30][CH3:31])[C:26]([CH3:32])=[CH:25][N:24]=2)[CH:12]=1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:7][CH2:8][C:9]#[C:10][C:11]1[C:19]2[C:18]([Cl:20])=[N:17][C:16]([NH2:21])=[N:15][C:14]=2[N:13]([CH2:22][C:23]2[C:28]([CH3:29])=[C:27]([O:30][CH3:31])[C:26]([CH3:32])=[CH:25][N:24]=2)[CH:12]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57713821HCID 57713821, compound

Product 1

HCID 57713851HCID 57713851, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of {3-[2-Amino-4-chloro-7-(4-methoxy-3,5-dimethyl-pyridin-2-ylmethyl)-7H-pyrrolo [2,3-d]pyrimidin-5-yl]-prop-2-ynyl}-carbamic acid tert-butyl ester (see previous example, 22 mg) in DCM (3 mL) was treated with TFA (0.6 mL) at rt for 15 min. Evaporation, work-up (DCM/sat. aq. NaHCO3), drying (Na2SO4), and evaporation gave the title compound as an oil. tR=3.85 min. 1H NMR (CDCl3) δ 8.24 (s, 1H), 7.06 (s, 1H), 5.32 (s, 2H), 5.02 (s, 2H), 3.75 (s, 3H), 2.27 (s, 3H), 2.20 (s, 3H).

Workup

  1. customEvaporation, work-up (DCM/sat. aq. NaHCO3)
  2. customdrying
  3. custom(Na2SO4), and evaporation

Sources & evidence

ORD record
ord-40de7b7278da4031a12c6ec89368dc94
Source dataset
uspto-grants-2012_01
Patent number
US08093229B2

Reaction notes

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