Trifluoroacetic acid → HCID 86677799, compound

HRID 1499873Notes

Reaction equation

HRID 1499873 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:12]([C:14]3[C:15]([O:34][CH3:35])=[C:16]([CH:23]4[CH2:26][N:25](C(OC(C)(C)C)=O)[CH2:24]4)[C:17]([C:21]#[N:22])=[C:18]([Cl:20])[CH:19]=3)[CH3:13])[N:9]=[C:10]([CH3:11])[C:3]=12.FC(F)(F)C(O)=O>C(Cl)Cl.CO.C(=O)(O)[O-].[Na+].[Cl-].[Na+].O>[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:12]([C:14]3[CH:19]=[C:18]([Cl:20])[C:17]([C:21]#[N:22])=[C:16]([CH:23]4[CH2:24][NH:25][CH2:26]4)[C:15]=3[O:34][CH3:35])[CH3:13])[N:9]=[C:10]([CH3:11])[C:3]=12

Participants

7

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86677800HCID 86677800, compound

Product 1

HCID 86677799HCID 86677799, compoundYield 106.6%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of tert-butyl 3-{3-[1-(4-amino-3-methyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-6-cyano-2-methoxyphenyl}azetidine-1-carboxylate (1.7 g, 3.3 mmol) in methylene chloride (30 mL) was treated with trifluoroacetic acid (20 mL) and stirred at room temperature for 20 min. The reaction mixture was concentrated to give a residue that was diluted with methanol (50 mL) and saturated sodium bicarbonate solution (50 mL). This aqueous solution was diluted with brine (50 mL) and extracted with a 5:1 mixture of dichloromethane/isopropanol (5×100 mL). The combined organic extracts were dried over sodium sulfate and concentrated to give the desired product (1.4 g, 97%). The product was isolated as a single enantiomer. 1H NMR (300 MHz, DMSO-d6) δ 8.11 (s, 1H), 7.46 (s, 1H), 7.34 (br s, 2H), 6.24 (q, J=6.9 Hz, 1H), 4.40-4.26 (m, 1H), 3.90-3.68 (m, 4H), 3.63 (s, 3H), 2.55 (s, 3H), 1.72 (d, J=7.1 Hz, 3H). LCMS for C19H21ClN7O (M+H)+: m/z=398.1; Found: 398.1.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customto give a residue that
  3. extractionextracted with a 5:1 mixture of dichloromethane/isopropanol (5×100 mL)
  4. dry with materialThe combined organic extracts were dried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9c2a2d8da8ac427180822563233a7ba8
Source dataset
uspto-grants-2015_12
Patent number
US09199982B2

Reaction notes

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