Acetic Acid → (S)-(1-(6-methyl-2-(methyl(4-(2-methyl-1H-imidazol-1-yl)phenyl)amino)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)indolin-2-yl)methanol

HRID 1930641노트

반응식

HRID 1930641 반응식
[CH3:1][C:2]1[N:3]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]3[N:15]=[C:16]([N:24]4[C:32]5[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=5)[CH2:26][C@H:25]4CO)[C:17]4[CH2:23][NH:22][CH2:21]C[C:18]=4[N:19]=3)=[CH:9][CH:8]=2)[CH:4]=[CH:5][N:6]=1.[C:35](O)(=O)[CH3:36].[CH2:39]=[O:40].[C:41]([BH3-])#N.[Na+]>CO>[CH3:21][N:22]1[CH2:36][CH2:35][C:18]2[N:19]=[C:14]([N:13]([CH3:41])[C:10]3[CH:9]=[CH:8][C:7]([N:3]4[CH:4]=[CH:5][N:6]=[C:2]4[CH3:1])=[CH:12][CH:11]=3)[N:15]=[C:16]([N:24]3[C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[CH2:26][C@H:25]3[CH2:39][OH:40])[C:17]=2[CH2:23]1

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 59333741(S)-(1-(2-(4-(2-Methyl-1H-imidazol-1-yl)phenylamino)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)indolin-2-yl)methanol

생성물 1

HCID 46199433(S)-(1-(6-methyl-2-(methyl(4-(2-methyl-1H-imidazol-1-yl)phenyl)amino)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)indolin-2-yl)methanol수율 27.9%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

(S)-(1-(2-(4-(2-Methyl-1H-imidazol-1-yl)phenylamino)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)indolin-2-yl)methanol (49 mg, 0.11 mmol) was dissolved in methanol (3 mL). Acetic acid (6.18 μL, 0.11 mmol) was added followed by formaldehyde (0.016 mL, 0.22 mmol). The reaction mixture was allowed to stirred at room temperature for 15 minutes and sodium cyanoborohydride (13.58 mg, 0.22 mmol) was added. After 1 h the solvent was evaporated and the crude dissolved in few drops of methanol, filtered and purified by preparative HPLC to give (S)-(1-(6-methyl-2-(methyl(4-(2-methyl-1H-imidazol-1-yl)phenyl)amino)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)indolin-2-yl)methanol (14.80 mg, 26.2%) and (S)-(1-(6-methyl-2-(4-(2-methyl-1H-imidazol-1-yl)phenylamino)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)indolin-2-yl)methanol (4.60 mg, 8.07%) were obtained as acetate salt.

후처리

  1. customAfter 1 h the solvent was evaporated
  2. dissolutionthe crude dissolved in few drops of methanol
  3. filtrationfiltered
  4. custompurified by preparative HPLC

출처 및 근거

ORD 기록
ord-02a6b51ab5cd46479b95c5a24a549bba
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08188101B2

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