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Potassium Hydroxide → N2-(1-(6-chloro-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)-N4-(5-cyclopropyl-1H-pyrazol-3-yl)pyrimidine-2,4-diamine

HRID 2409072
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HRID 2409072 반응식
[Cl:1][C:2]1[CH:3]=[C:4]2[N:28](S(C3C=CC(C)=CC=3)(=O)=O)[CH:27]=[CH:26][C:5]2=[N:6][C:7]=1[CH:8]([NH:10][C:11]1[N:16]=[C:15]([NH:17][C:18]2[CH:22]=[C:21]([CH:23]3[CH2:25][CH2:24]3)[NH:20][N:19]=2)[CH:14]=[CH:13][N:12]=1)[CH3:9].[OH-].[K+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]2[NH:28][CH:27]=[CH:26][C:5]2=[N:6][C:7]=1[CH:8]([NH:10][C:11]1[N:16]=[C:15]([NH:17][C:18]2[CH:22]=[C:21]([CH:23]3[CH2:24][CH2:25]3)[NH:20][N:19]=2)[CH:14]=[CH:13][N:12]=1)[CH3:9]
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참가 물질

4

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HCID 14797Potassium HydroxideHCID 86689873N2-(1-(6-chloro-1-tosyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)-N4-(5-cyclopropyl-1H-pyrazol-3-yl)pyrimidine-2,4-diamine

생성물 1

HCID 71611845N2-(1-(6-chloro-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)-N4-(5-cyclopropyl-1H-pyrazol-3-yl)pyrimidine-2,4-diamine수율 26%

시약·촉매·용매 1

HCID 887Methanol용매

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온도
100 °C

실험 절차

To a solution of N2-(1-(6-chloro-1-tosyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)-N4-(5-cyclopropyl-1H-pyrazol-3-yl)pyrimidine-2,4-diamine (320 mg, 0.58 mmol) in methanol (5 mL) was added an aqueous solution of KOH (2 N, 5 mL). The mixture was heated at 100° C. for 3 h. The reaction mixture was quenched with a saturated NH4Cl solution and extracted with EtOAc. The extract was washed with H2O, dried (Na2SO4), filtered, and concentrated under reduced pressure. The crude product was purified by preparative HPLC to afford 30 mg (26%) of N2-(1-(6-chloro-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)-N4-(5-cyclopropyl-1H-pyrazol-3-yl)pyrimidine-2,4-diamine as white solid. 1H NMR (500 MHz, CD3OD): δ 11.93 (s, 1H), 11.41 (s, 1H), 9.40 (m, 1H), 7.80 (d, 2H), 7.69 (s, 1H), 6.60 (m, 2H), 6.27 (d, 2H), 5.63 (m, 1H), 1.88 (s, 1H), 1.45 (d, 3H), 0.94 (m, 2H), 0.71 (m, 2H); MS (ESI): m/z=395.1 [M+1]+.

후처리

  1. customThe reaction mixture was quenched with a saturated NH4Cl solution
  2. extractionextracted with EtOAc
  3. washThe extract was washed with H2O
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by preparative HPLC

출처 및 근거

ORD 기록
ord-b56d924bed254d4cbe51f2e70ab85e9d
출처 데이터셋
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08815877B2

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