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Acetaldehyde → N-(5-Bromo-pyridin-2-yl)-3-(7-isopropyl-pyrido[2,3-d]pyrimidin-4-ylamino)-4-[4-(ethyl-propyl-amino)-phenylsulfanyl]-benzamide

HRID 605328
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HRID 605328 반응식
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:41])[C:10]2[CH:15]=[CH:14][C:13]([S:16][C:17]3[CH:22]=[CH:21][C:20]([NH:23][CH2:24][CH2:25][CH3:26])=[CH:19][CH:18]=3)=[C:12]([NH:27][C:28]3[C:29]4[CH:37]=[CH:36][C:35]([CH:38]([CH3:40])[CH3:39])=[N:34][C:30]=4[N:31]=[CH:32][N:33]=3)[CH:11]=2)=[N:6][CH:7]=1.[C:42](O[BH-](OC(=O)C)OC(=O)C)(=O)[CH3:43].[Na+].C(=O)C>ClCCl.CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:41])[C:10]2[CH:15]=[CH:14][C:13]([S:16][C:17]3[CH:18]=[CH:19][C:20]([N:23]([CH2:42][CH3:43])[CH2:24][CH2:25][CH3:26])=[CH:21][CH:22]=3)=[C:12]([NH:27][C:28]3[C:29]4[CH:37]=[CH:36][C:35]([CH:38]([CH3:40])[CH3:39])=[N:34][C:30]=4[N:31]=[CH:32][N:33]=3)[CH:11]=2)=[N:6][CH:7]=1
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참가 물질

5

반응물 3

HCID 177AcetaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 67041086N-(5-Bromo-pyridin-2-yl)-3-(7-isopropyl-pyrido[2,3-d]pyrimidin-4-ylamino)-4-(4-propylamino-phenylsulfanyl)-benzamide

생성물 1

HCID 67040430N-(5-Bromo-pyridin-2-yl)-3-(7-isopropyl-pyrido[2,3-d]pyrimidin-4-ylamino)-4-[4-(ethyl-propyl-amino)-phenylsulfanyl]-benzamide수율 77%

시약·촉매·용매 1

HCID 21226129
Dichloromethane methanol
용매

실험 절차

To the product of Example 378 (31 mg, 0.05 mmol) and sodium triacetoxyborohydride (414 mg, 2.0 mmol) in dichloromethane/methanol (5 mL, 9:1) was added acetaldehyde (112 μL, 2.0 mmol). The mixture was stirred at room temperature for 16 hours and evaporated. The residue was partitioned between saturated sodium carbonate solution and ethyl acetate. The organic layer was washed with water, dried with magnesium sulfate, filtered and evaporated. The residue was purified by silica gel chromatography eluting with dichloromethane/methanol (99:1) to give the title compound (25 mg, 77%). 1H NMR (300 MHz, DMSO-D6) δ ppm: 0.90 (t, J=7.35 Hz, 3 H) 1.09 (t, J=6.99 Hz, 3 H) 1.34 (d, J=6.99 Hz, 6 H) 1.55 (m, 2 H) 3.24 (m, 3 H) 3.38 (q, J=6.99 Hz, 2 H) 6.71 (d, J=8.82 Hz, 2 H) 6.87 (d, J=8.82 Hz, 1 H) 7.26 (d, J=8.82 Hz, 2 H) 7.63 (d, J=8.46 Hz, 1 H) 7.88 (d, J=8.46 Hz, 1 H) 8.04 (d, J=2.57 Hz, 1 H) 8.07 (d, J=2.21 Hz, 1 H) 8.17 (m, 1 H) 8.49 (d, J=1.84 Hz, 1 H) 8.58 (s, 1 H) 8.89 (d, J=8.46 Hz, 1 H) 10.13 (s, 1 H) 10.91 (s, 1 H); (ESI+) m/z 656, 658 (M+H)+.

후처리

  1. customevaporated
  2. customThe residue was partitioned between saturated sodium carbonate solution and ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried with magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by silica gel chromatography
  8. washeluting with dichloromethane/methanol (99:1)

출처 및 근거

ORD 기록
ord-ac6f82e0f3a64e55b797af0c8467ade9
출처 데이터셋
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07910595B2

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