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Sodium Chloride → (R)-tert-butyl 2-(5-amino-4-(8-fluorochroman-4-ylamino)pyrimidin-2-ylamino)-4-fluorophenylcarbamate

HRID 1363171
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HRID 1363171 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[C:4]([NH:16][C:17]2[N:22]=[C:21]([NH:23][C@H:24]3[C:33]4[C:28](=[C:29]([F:34])[CH:30]=[CH:31][CH:32]=4)[O:27][CH2:26][CH2:25]3)[C:20]([N+:35]([O-])=O)=[CH:19][N:18]=2)[CH:3]=1.S(S([O-])=O)([O-])=O.[Na+].[Na+].C(=O)(O)[O-].[Na+].[Cl-].[Na+]>C1COCC1.O.CO>[NH2:35][C:20]1[C:21]([NH:23][C@H:24]2[C:33]3[C:28](=[C:29]([F:34])[CH:30]=[CH:31][CH:32]=3)[O:27][CH2:26][CH2:25]2)=[N:22][C:17]([NH:16][C:4]2[CH:3]=[C:2]([F:1])[CH:7]=[CH:6][C:5]=2[NH:8][C:9](=[O:15])[O:10][C:11]([CH3:13])([CH3:14])[CH3:12])=[N:18][CH:19]=1
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참가 물질

8

반응물 4

HCID 5234Sodium ChlorideHCID 24489Sodium DithioniteHCID 516892Sodium BicarbonateHCID 66970500(R)-tert-Butyl 4-fluoro-2-(4-(8-fluorochroman-4-ylamino)-5-nitropyrimidin-2-ylamino)phenylcarbamate

생성물 1

HCID 66970669(R)-tert-butyl 2-(5-amino-4-(8-fluorochroman-4-ylamino)pyrimidin-2-ylamino)-4-fluorophenylcarbamate

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of (R)-tert-butyl 4-fluoro-2-(4-(8-fluorochroman-4-ylamino)-5-nitropyrimidin-2-ylamino)phenylcarbamate (141 mg) in THF (20 mL) was added a premixed solution of sodium hydrosulfite (0.6 g) and sodium bicarbonate (0.3 g) in water (50 mL). MeOH (5 mL) was also added to aid solution of the mixture, which was stirred at room temperature for 30 min, when sodium chloride was added to saturate the solution. The resultant mixture was extracted with EtOAc (2×), the combined organics were dried, filtered and evaporated to yield (R)-tert-butyl 2-(5-amino-4-(8-fluorochroman-4-ylamino)pyrimidin-2-ylamino)-4-fluorophenylcarbamate that was used as such for the next step, MH+=485.

후처리

  1. concentrationto saturate the solution
  2. extractionThe resultant mixture was extracted with EtOAc (2×)
  3. customthe combined organics were dried
  4. filtrationfiltered
  5. customevaporated

출처 및 근거

ORD 기록
ord-948eeca788b94a2b9c0354792a653eda
출처 데이터셋
uspto-grants-2011_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07884109B2

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