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Hydrochloric Acid → imino-methyl-[1-[6-[(3R)-3-methylmorpholin-4-yl]-2-(1H-pyrrolo[2,3-b]pyridin-4-yl)pyrimidin-4-yl]cyclopropyl]-oxo-lambda6-sulfane

HRID 1484041
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HRID 1484041 반응식
[OH-].[Na+].[CH3:3][C@@H:4]1[CH2:9][O:8][CH2:7][CH2:6][N:5]1[C:10]1[CH:15]=[C:14]([C:16]2([S:19]([CH3:22])(=[NH:21])=[O:20])[CH2:18][CH2:17]2)[N:13]=[C:12]([C:23]2[CH:28]=[CH:27][N:26]=[C:25]3[N:29](S(C4C=CC(C)=CC=4)(=O)=O)[CH:30]=[CH:31][C:24]=23)[N:11]=1.O.Cl>COCCOC>[CH3:3][C@@H:4]1[CH2:9][O:8][CH2:7][CH2:6][N:5]1[C:10]1[CH:15]=[C:14]([C:16]2([S:19]([CH3:22])(=[NH:21])=[O:20])[CH2:18][CH2:17]2)[N:13]=[C:12]([C:23]2[CH:28]=[CH:27][N:26]=[C:25]3[NH:29][CH:30]=[CH:31][C:24]=23)[N:11]=1
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참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 86660216(3R)-3-methyl-4-(6-(1-(S-methylsulfonimidoyl)cyclopropyl)-2-(1-tosyl-1H-pyrrolo[2,3-b]pyridin-4-yl)pyrimidin-4-yl)morpholine

생성물 1

HCID 86660217imino-methyl-[1-[6-[(3R)-3-methylmorpholin-4-yl]-2-(1H-pyrrolo[2,3-b]pyridin-4-yl)pyrimidin-4-yl]cyclopropyl]-oxo-lambda6-sulfane
수율 60.3%

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane용매

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온도
50 °C

실험 절차

In a separate experiment, NaOH, 2M aqueous solution (7.60 ml, 15.19 mmol) was added to (3R)-3-methyl-4-(6-(1-(S-methylsulfonimidoyl)cyclopropyl)-2-(1-tosyl-1H-pyrrolo[2,3-b]pyridin-4-yl)pyrimidin-4-yl)morpholine (4.92 g, 8.68 mmol) in DME (100 ml)/water (25.00 ml). The resulting solution was stirred at 50° C. for 18 hours. The reaction mixture was acidified with 2M HCl (˜5 mL) to pH5. The reaction mixture was evaporated and the residue was dissolved in DCM (250 ml) and washed with water (200 ml). The organic layer was dried over MgSO4, filtered and then evaporated to approximately 50 ml in volume. The resulting solution was purified by flash chromatography on silica, eluting with a gradient of 0 to 7% MeOH in DCM. Pure fractions were evaporated to dryness to afford 4-{4-[(3R)-3-methylmorpholin-4-yl]-6-[1-(S-methylsulfonimidoyl)cyclopropyl]pyrimidin-2-yl}-1H-pyrrolo[2,3-b]pyridine (2.160 g, 60%); 1H NMR (400 MHz, DMSO-d6) 1.28 (3H, d), 1.41-1.59 (3H, m), 1.76 (1H, dt), 3.10 (3H, d), 3.31 (1H, d), 3.52 (1H, t), 3.67 (1H, dd), 3.80 (2H, d), 4.01 (1H, dd), 4.21 (1H, d), 4.58 (1H, s), 7.00 (1H, d), 7.22 (1H, dd), 7.54-7.63 (1H, m), 7.95 (1H, d), 8.33 (1H, d), 11.75 (1H, s); m/z: (ES+) MH+, 413.19.

후처리

  1. customThe reaction mixture was evaporated
  2. dissolutionthe residue was dissolved in DCM (250 ml)
  3. washwashed with water (200 ml)
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. customevaporated to approximately 50 ml in volume
  7. customThe resulting solution was purified by flash chromatography on silica
  8. washeluting with a gradient of 0 to 7% MeOH in DCM
  9. customPure fractions were evaporated to dryness

출처 및 근거

ORD 기록
ord-37c2af8eb80b4299b6b2a2fb138178a3
출처 데이터셋
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09421213B2

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