Trifluoroacetic acid → HCID 86714523, compound

HRID 1851035Notes

Reaction equation

HRID 1851035 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH2:25][C@H:26]3[CH2:30][CH2:29][CH2:28][N:27]3[C:31](=[O:47])/[C:32](/[C:45]#[N:46])=[CH:33]/[C:34]([NH:37]C(=O)OC(C)(C)C)([CH3:36])[CH3:35])[N:9]=[C:10]([C:11]3[CH:16]=[CH:15][C:14]([O:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[CH:13][C:12]=3[F:24])[C:3]=12.[F:48][C:49]([F:54])([F:53])[C:50]([OH:52])=[O:51]>C(Cl)Cl>[F:48][C:49]([F:54])([F:53])[C:50]([OH:52])=[O:51].[F:48][C:49]([F:54])([F:53])[C:50]([OH:52])=[O:51].[F:48][C:49]([F:54])([F:53])[C:50]([OH:52])=[O:51].[NH2:37][C:34]([CH3:36])([CH3:35])[CH:33]=[C:32]([C:31]([N:27]1[CH2:28][CH2:29][CH2:30][C@@H:26]1[CH2:25][N:8]1[C:4]2=[N:5][CH:6]=[N:7][C:2]([NH2:1])=[C:3]2[C:10]([C:11]2[CH:16]=[CH:15][C:14]([O:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:13][C:12]=2[F:24])=[N:9]1)=[O:47])[C:45]#[N:46]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86714525HCID 86714525, compound

Product 1

HCID 86714523HCID 86714523, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R,E)-tert-butyl (5-(2-((4-amino-3-(2-fluoro-4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)pyrrolidin-1-yl)-4-cyano-2-methyl-5-oxopent-3-en-2-yl)carbamate (90 mg, 0.14 mmol, 1 equiv) in 16 mL DCM was added 4 mL trifluoroacetic acid dropwise. The resulting solution was stirred for 3 h at room temperature. The solution was concentrated under reduced pressure. The residue was purified on Prep-HPLC. Conditions: (1#-Pre-HPLC-001(SHIMADZU)): Column, SunFire Prep C18, 19*150 mm Sum; mobile phase, water with 0.05% TFA and CH3CN (40% CH3CN up to 100% in 20 min); Detector, 254 nm to give the title compound as a pale light yellow solid.

Workup

  1. concentrationThe solution was concentrated under reduced pressure
  2. customThe residue was purified on Prep-HPLC
  3. waitmobile phase, water with 0.05% TFA and CH3CN (40% CH3CN up to 100% in 20 min)

Sources & evidence

ORD record
ord-7a83b20ae8f8455aba0772994fc73058
Source dataset
uspto-grants-2015_02
Patent number
US08957080B2

Reaction notes

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