Water → HCID 11584138, compound

HRID 550494Notes

Reaction equation

HRID 550494 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:16][C:17]2[N:22]=[CH:21][N:20]=[C:19]3[NH:23][N:24]=[C:25]([O:26][CH2:27][CH2:28][NH:29][CH2:30][CH2:31][OH:32])[C:18]=23)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1.[C:33](OC(=O)C)(=[O:35])[CH3:34].O>CC(N(C)C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([NH:16][C:17]2[N:22]=[CH:21][N:20]=[C:19]3[NH:23][N:24]=[C:25]([O:26][CH2:27][CH2:28][N:29]([CH2:30][CH2:31][OH:32])[C:33](=[O:35])[CH3:34])[C:18]=23)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 11532615HCID 11532615, compound

Product 1

HCID 11584138HCID 11584138, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
-15 °C

Procedure

2-({2-[(4-{[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]amino}-1H-pyrazolo[3,4-d]pyrimidin-3-yl)oxy]ethyl}amino)ethanol (prepared as described in Example 36/30 mg, 0.07 mmol) was dissolved in DMA and the mixture was cooled to −15° C. Acetic anhydride (6 μL, 0.07 mmol) was added and the mixture was stirred for 1 hour. Water was then added and the precipitated solid was filtered and dried to give the title compound (22 mg, 67%); NMR Spectrum (mixture of rotamers): (major isomer) 2.08 (s, 3H), 3.49 (t, 2H), 3.56-3.59 (m, 2H), 3.80 (t, 2H), 4.40 (t, 2H), 4.90 (t, 1H), 5.28 (s, 2H), 7.26 (d, 1H), 7.37 (t, 1H), 7.58 (d, 1H), 7.84-7.98 (m, 2H), 8.16 (d, 1H), 8.28 (s, 1H), 8.30 (s, 1H), 8.59 (d, 1H); Mass Spectrum: 498 (MH+).

Workup

  1. filtrationthe precipitated solid was filtered
  2. customdried

Sources & evidence

ORD record
ord-489f8e3e6db9430abc93fc6ff6b10652
Source dataset
uspto-grants-2011_05
Patent number
US07947676B2

Reaction notes

Loading…