Sodium Hydroxide → 4-[2-((R)-1-tert-Butoxycarbonyl-piperidin-3-yloxy)-4-fluoro-Phenylamino]-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylic acid

HRID 240628노트

반응식

HRID 240628 반응식
C[O:2][C:3]([C:5]1[S:35][C:8]2[N:9]=[CH:10][N:11]=[C:12]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=3[O:21][C@@H:22]3[CH2:27][CH2:26][CH2:25][N:24]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:23]3)[C:7]=2[C:6]=1[CH3:36])=[O:4].[OH-].[Na+]>CO.C1COCC1>[C:31]([O:30][C:28]([N:24]1[CH2:25][CH2:26][CH2:27][C@@H:22]([O:21][C:15]2[CH:16]=[C:17]([F:20])[CH:18]=[CH:19][C:14]=2[NH:13][C:12]2[C:7]3[C:6]([CH3:36])=[C:5]([C:3]([OH:4])=[O:2])[S:35][C:8]=3[N:9]=[CH:10][N:11]=2)[CH2:23]1)=[O:29])([CH3:34])([CH3:32])[CH3:33]

참가 물질

4

반응물 2

HCID 14798Sodium HydroxideHCID 584131274-[2-((R)-1-tert-Butoxycarbonyl-piperidin-3-yloxy)-4-fluoro-phenylamino]-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylic acid methyl ester

생성물 1

HCID 584130574-[2-((R)-1-tert-Butoxycarbonyl-piperidin-3-yloxy)-4-fluoro-Phenylamino]-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylic acid

시약·촉매·용매 1

HCID 21899815MeOH tetrahydrofuran용매

실험 절차

A mixture of 4-[2-((R)-1-tert-Butoxycarbonyl-piperidin-3-yloxy)-4-fluoro-phenylamino]-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylic acid methyl ester (1.65 g) in MeOH/THF (1:1; 20 ml) was treated with NaOH (2M; 8 ml) and heated at reflux for 10 mins. Organic solvent was removed in vacuo. HCl (2M; 8 ml) was added to pH 1 and water was added. The suspension was filtered and washed with water. The solid was suspended in EtOH and evaporated. The residue was triturated with Acetonitrile to give the desired product.

후처리

  1. temperatureheated
  2. temperatureat reflux for 10 mins
  3. customOrganic solvent was removed in vacuo
  4. additionHCl (2M; 8 ml) was added to pH 1 and water
  5. additionwas added
  6. filtrationThe suspension was filtered
  7. washwashed with water
  8. customevaporated
  9. customThe residue was triturated with Acetonitrile

출처 및 근거

ORD 기록
ord-0cce96f0b7684110914f88a568983c6f
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08648068B2

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