Triethylamine → Cyclopentyl-{4-[4-(6-fluoro-pyrido[3,4-d]pyrimidin-4-ylamino)-2-methyl-phenoxy]-piperidin-1-yl}-methanone

HRID 731905노트

반응식

HRID 731905 반응식
[CH:1]1([C:6](Cl)=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.[F:9][C:10]1[N:34]=[CH:33][C:13]2[N:14]=[CH:15][N:16]=[C:17]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([O:25][CH:26]4[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]4)=[C:21]([CH3:32])[CH:20]=3)[C:12]=2[CH:11]=1.CCN(CC)CC>C(Cl)Cl>[CH:1]1([C:6]([N:29]2[CH2:28][CH2:27][CH:26]([O:25][C:22]3[CH:23]=[CH:24][C:19]([NH:18][C:17]4[C:12]5[CH:11]=[C:10]([F:9])[N:34]=[CH:33][C:13]=5[N:14]=[CH:15][N:16]=4)=[CH:20][C:21]=3[CH3:32])[CH2:31][CH2:30]2)=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 78284Cyclopentanecarbonyl chlorideHCID 69051976(6-Fluoro-pyrido[3,4-d]pyrimidin-4-yl)-[3-methyl-4-(piperidin-4-yloxy)-phenyl]-amine

생성물 1

HCID 69051928Cyclopentyl-{4-[4-(6-fluoro-pyrido[3,4-d]pyrimidin-4-ylamino)-2-methyl-phenoxy]-piperidin-1-yl}-methanone수율 70%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Cyclopentane carbonyl chloride (0.187 g, 1.41 mmol) was added to a solution of (6-Fluoro-pyrido[3,4-d]pyrimidin-4-yl)-[3-methyl-4-(piperidin-4-yloxy)-phenyl]-amine (T) (0.50 g, 1.28 mmol) and NEt3 (0.38 g, 3.84 mmol) in CH2Cl2 (15 mL After 1 h the reaction was quenched with water, the layers were separated and the organic layer was washed with 1N NaOH and water, dried over Na2SO4, and concentrated. Purification by flash column chromatography (CH2Cl2/MeOH, 97/3) afforded the title compound as a yellow solid (0.40 g, 70%). LRMS: 450.3 (MH+); 1H NMR (DMSO-d6, 400 MHz): δ 9.90 (s, 1H), δ 8.86 (s, 1H), δ 8.58 (s, 1H), δ 8.19 (s, 1H), δ 7.54-7.56 (m, 2H), δ 7.04 (d, J=9.56 Hz, 1H) δ 4.58-4.61 (m, 1H), δ 3.70-3.72 (m, 2H), δ 3.33-3.44 (m, 2H), δ 2.93-3.008 (m, 1H), δ 2.17 (s, 3H), δ 1.46-1.94 (m, 12H).

후처리

  1. customwas quenched with water
  2. customthe layers were separated
  3. washthe organic layer was washed with 1N NaOH and water
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customPurification by flash column chromatography (CH2Cl2/MeOH, 97/3)

출처 및 근거

ORD 기록
ord-260bdb28b711417dbf25184766b98c68
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07585869B2

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