Trifluoroacetic acid methylene chloride → HCID 56932263, compound

HRID 577276Notes

Reaction equation

HRID 577276 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][N:21]3[C:25]4=[N:26][C:27]([NH:30][C:31]5[CH:32]=[N:33][N:34]([CH3:36])[CH:35]=5)=[N:28][CH:29]=[C:24]4[CH:23]=[N:22]3)[CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O.C(Cl)Cl>>[CH3:36][N:34]1[CH:35]=[C:31]([NH:30][C:27]2[N:26]=[C:25]3[N:21]([CH2:20][C:16]4[CH:17]=[CH:18][CH:19]=[C:14]([N:11]5[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]5)[CH:15]=4)[N:22]=[CH:23][C:24]3=[CH:29][N:28]=2)[CH:32]=[N:33]1

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 68378875HCID 68378875, compound

Product 1

HCID 56932263HCID 56932263, compoundYield 12%

Procedure

tert-Butyl-4-(3-((6-((1-methyl-1H-pyrazol-4-yl)amino)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)phenyl)piperazine-1-carboxylate (1.10 g, 2.25 mmol) was treated with TFA/DCM (1:2, 12 mL) for 1 h at rt. After evaporation to dryness, the residue was purified by preparative HPLC to afford the title compound (103 mg, 0.26 mmol, 12% over two steps). 1H NMR (d6-DMSO) δ 9.83 (s, 1H), 8.90 (s, 1H), 8.08 (s, 1H), 8.04 (s, 1H), 7.58 (s, 1H), 7.18-7.06 (m, 1H), 7.00 (s, 1H), 6.84-6.75 (m, 1H), 6.73-6.58 (m, 1H), 5.48 (s, 2H), 3.84 (s, 3H), 2.99-2.91 (m, 4H), 2.79-2.71 (m, 4H), 2.22 (br s, 1H); LC-MS method B, (ES+) 390.1, RT=4.93 min.

Workup

  1. customAfter evaporation to dryness
  2. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-67f1cac968b84168bf0b9f7b3260bad0
Source dataset
uspto-grants-2015_05
Patent number
US09040545B2

Reaction notes

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