Aniline → HCID 58836884, compound

HRID 2357993Notes

Reaction equation

HRID 2357993 reaction equation
Cl[C:2]1[N:7]=[C:6]2[N:8]([CH2:20][CH2:21][CH:22]3[CH2:27][CH2:26][N:25](C(OC(C)(C)C)=O)[CH2:24][CH2:23]3)[N:9]=[C:10]([NH:11][C:12]3[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][C:13]=3[Cl:19])[C:5]2=[CH:4][N:3]=1.[NH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.C(O)(C(F)(F)F)=O>O1CCOCC1>[Cl:18][C:17]1[CH:16]=[CH:15][CH:14]=[C:13]([Cl:19])[C:12]=1[NH:11][C:10]1[C:5]2[C:6](=[N:7][C:2]([NH:35][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)=[N:3][CH:4]=2)[N:8]([CH2:20][CH2:21][CH:22]2[CH2:23][CH2:24][NH:25][CH2:26][CH2:27]2)[N:9]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 6422Trifluoroacetic acidHCID 58836886HCID 58836886, compound

Product 1

HCID 58836884HCID 58836884, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 48.5 mg (0.09 mmol) of tert-butyl 4-(2-(6-chloro-3-(2,6-dichlorophenylamino)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)piperidine-1-carboxylate 93 in 5 mL 1,4-dioxane was treated sequentially with 17 μl (0.2 mmol) of aniline and 525 μl (7.1 mmol) of TFA. The resulting orange solution was heated at reflux for 22 h, and then was concentrated. The residue was purified by chromatography on silica gel (CH2Cl2:MeOH, 9:1) to give the title compound 94. 1H-NMR (CD3OD) δ 1.22-1.45 (m, 3H), 1.66-1.78 (m, 2H), 1.91-2.02 (m, 2H), 2.10 (s, 1H), 2.62-2.74 (m, 2H), 3.10-3.23 (m, 2H), 4.15 (t, J=6.3 Hz, 2H), 6.99 (t, J=8.0 Hz, 1H), 7.19 (t, J=8.1 Hz, 1H), 7.23-7.31 (m, 2H), 7.42 (t, J=8.5 Hz, 2H), 7.71 (d, J=8.5 Hz, 2H), 8.56 (s, 1H). Mass Spectrum (ESI) m/e=482.0 (M+1).

Workup

  1. temperatureThe resulting orange solution was heated
  2. temperatureat reflux for 22 h
  3. concentrationwas concentrated
  4. customThe residue was purified by chromatography on silica gel (CH2Cl2:MeOH, 9:1)

Sources & evidence

ORD record
ord-cfcab53cfcb84bc98df381b0be526e49
Source dataset
uspto-grants-2010_07
Patent number
US07763624B2

Reaction notes

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