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 550492ノート

反応式

HRID 550492 の反応式
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

参加物

6

反応物 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

生成物 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-methylacetamide収率 99.8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-9fae53fb6d364a0bb2fcf9a70336d81b
出典データセット
uspto-grants-2011_05
特許番号
US07947676B2

反応ノート

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