Triethylamine → 1-((4-methyl-1-(2-(1-methyl-1H-indazol-5-ylamino)pyrimidin-4-yl)-1H-pyrrol-3-yl)methyl)azetidin-3-ol

HRID 539903노트

반응식

HRID 539903 반응식
[CH3:1][C:2]1[C:3]([CH:24]=O)=[CH:4][N:5]([C:7]2[CH:12]=[CH:11][N:10]=[C:9]([NH:13][C:14]3[CH:15]=[C:16]4[C:20](=[CH:21][CH:22]=3)[N:19]([CH3:23])[N:18]=[CH:17]4)[N:8]=2)[CH:6]=1.Cl.[NH:27]1[CH2:30][CH:29]([OH:31])[CH2:28]1.C(N(CC)CC)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCl>[CH3:1][C:2]1[C:3]([CH2:24][N:27]2[CH2:30][CH:29]([OH:31])[CH2:28]2)=[CH:4][N:5]([C:7]2[CH:12]=[CH:11][N:10]=[C:9]([NH:13][C:14]3[CH:15]=[C:16]4[C:20](=[CH:21][CH:22]=3)[N:19]([CH3:23])[N:18]=[CH:17]4)[N:8]=2)[CH:6]=1

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 27592903-Hydroxyazetidine hydrochlorideHCID 5049666Sodium triacetoxyborohydrideHCID 866989924-methyl-1-(2-(1-methyl-1H-indazol-5-ylamino)pyrimidin-4-yl)-1H-pyrrole-3-carbaldehyde

생성물 1

HCID 866989941-((4-methyl-1-(2-(1-methyl-1H-indazol-5-ylamino)pyrimidin-4-yl)-1H-pyrrol-3-yl)methyl)azetidin-3-ol

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a slurry of intermediate 13 (0.45 g, 1.3 mmol), 3-azetidinol hydrochloride (0.3 g, 2.7 mmol) and triethylamine (0.76 mL) in 50 mL of dichloromethane, was added NaBH(OAc)3 (0.86 g, 4.5 mmol) at room temperature. The reaction was stirred for 12 hour at room temperature and then quenched with 1N—NaOH. It was extracted with dichloromethane (×2) and washed with brine. The collected organic layers were dried over anhydrous sodium sulfate and then concentrated in vacuo. The resulting residue was purified by column chromatography to afford desired Compound No. 143 as a pale yellow solid (0.27 g, 51%); MS (ESI) m/z 391 [M+H]+.]+; 1H NMR (300 MHz, DMSO-d6) δ 9.75 (s, 1H), 8.48 (d, 1H, J=5.4 Hz), 8.30 (s, 1H), 8.21 (s, 1H), 7.99 (s, 1H), 7.62 (m, 2H), 7.12 (d, 1H, J=5.4 Hz), 5.34 (m, 1H), 4.19 (m, 1H), 4.04 (s, 3H), 3.49 (m, 2H), 3044 (s, 2H), 2.77 (m, 2H), 2.29 (m, 3H).

후처리

  1. customquenched with 1N—NaOH
  2. extractionIt was extracted with dichloromethane (×2)
  3. washwashed with brine
  4. dry with materialThe collected organic layers were dried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-f151782efeec41cea1987a6a0a475799
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08871778B2

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