Glycolic Acid → N-(2-{[4-({3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}amino)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]oxy}ethyl)-2-hydroxy-N-methylacetamide

HRID 550492Notes

Reaction equation

HRID 550492 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[Cl:25][C:26]1[CH:27]=[C:28]([NH:41][C:42]2[N:47]=[CH:46][N:45]=[C:44]3[NH:48][N:49]=[C:50]([O:51][CH2:52][CH2:53][NH:54][CH3:55])[C:43]=23)[CH:29]=[CH:30][C:31]=1[O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[C:36]([F:40])[CH:35]=1.[C:56]([OH:60])(=O)[CH2:57][OH:58].CCN(C(C)C)C(C)C>CN(C=O)C>[Cl:25][C:26]1[CH:27]=[C:28]([NH:41][C:42]2[N:47]=[CH:46][N:45]=[C:44]3[NH:48][N:49]=[C:50]([O:51][CH2:52][CH2:53][N:54]([CH3:55])[C:56](=[O:60])[CH2:57][OH:58])[C:43]=23)[CH:29]=[CH:30][C:31]=1[O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[C:36]([F:40])[CH:35]=1

Participants

6

Reactant 4

HCID 757Glycolic AcidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 11611980N-{3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}-3-[2-(methylamino)ethoxy]-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Product 1

HCID 11526217N-(2-{[4-({3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}amino)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]oxy}ethyl)-2-hydroxy-N-methylacetamideYield 99.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

HATU (52 mg) was added to a stirred solution of N-{3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}-3-[2-(methylamino)ethoxy]-1H-pyrazolo[3,4-d]pyrimidin-4-amine (prepared as described in Example 60/47 mg, 0.10 mmol), glycolic acid (10 mg, 0.13 mmol) and DIPEA (60 μl) in DMF (4 ml) and the solution was stirred overnight. The reaction mixture was concentrated in vacuo and the residue partitioned between water and DCM. Organic extracts were dried and concentrated and the residue triturated with ether to give the title compound as a white solid (50 mg, 94%); Mass Spectrum 500.8 (M+/retention time 2.18 minutes).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue partitioned between water and DCM
  3. customOrganic extracts were dried
  4. concentrationconcentrated
  5. customthe residue triturated with ether

Sources & evidence

ORD record
ord-9fae53fb6d364a0bb2fcf9a70336d81b
Source dataset
uspto-grants-2011_05
Patent number
US07947676B2

Reaction notes

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