Hydrochloric Acid → 4-[(3-aminocyclobutyl)oxy]-2-[(1-methyl-1H-pyrazol-4-yl)amino]-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

HRID 577678노트

반응식

HRID 577678 반응식
[C:1]([C:3]1[C:11]2[C:10]([O:12][CH:13]3[CH2:16][CH:15]([NH:17]C(=O)OC(C)(C)C)[CH2:14]3)=[N:9][C:8]([NH:25][C:26]3[CH:27]=[N:28][N:29]([CH3:31])[CH:30]=3)=[N:7][C:6]=2[N:5]([CH2:32][O:33][CH2:34][CH2:35][Si:36]([CH3:39])([CH3:38])[CH3:37])[CH:4]=1)#[N:2].Cl>C(Cl)Cl>[NH2:17][CH:15]1[CH2:14][CH:13]([O:12][C:10]2[C:11]3[C:3]([C:1]#[N:2])=[CH:4][N:5]([CH2:32][O:33][CH2:34][CH2:35][Si:36]([CH3:39])([CH3:38])[CH3:37])[C:6]=3[N:7]=[C:8]([NH:25][C:26]3[CH:27]=[N:28][N:29]([CH3:31])[CH:30]=3)[N:9]=2)[CH2:16]1

참가 물질

4

반응물 2

HCID 313Hydrochloric AcidHCID 86679623tert-butyl {3-[(5-cyano-2-[(1-methyl-1H-pyrazol-4-yl)amino]-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)oxy]cyclobutyl}carbamate

생성물 1

HCID 866796244-[(3-aminocyclobutyl)oxy]-2-[(1-methyl-1H-pyrazol-4-yl)amino]-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile수율 99%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of tert-butyl {3-[(5-cyano-2-[(1-methyl-1H-pyrazol-4-yl)amino]-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)oxy]cyclobutyl}carbamate (cis:trans (1:1), 470 mg, 0.85 mmol) in DCM (20 mL) was added HCl (0.85 mL of 4 M in 1,4-dioxane, 3.4 mmol). After 20 hrs, the volatiles were removed and the reaction mixture was partitioned between DCM (50 mL) and saturated aqueous NaHCO3 (20 mL). The organic layer was separated, dried over Na2SO4 and evaporated to give the title compound (380 mg, 99% yield) as a 1:1 cis:trans isomeric mixture. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.41 (d, J=12.59 Hz, 1H) 8.10 (s, 1H) 7.96 (br. s., 1H) 7.55 (s, 1H) 5.53 (br. s., 2H) 3.82 (s, 3H) 3.61-3.73 (m, 1H) 3.52-3.60 (m, 4H) 3.04 (br. s., 1H) 2.71-2.85 (m, 1H) 2.15-2.40 (m, 2H) 1.76-1.92 (m, 1H) 0.76-0.91 (m, 1H) −0.12 (br. s., 9H). m/z (APCI+) for C21H30N8O2Si 455.1 (M+H)+.

후처리

  1. customthe volatiles were removed
  2. customthe reaction mixture was partitioned between DCM (50 mL) and saturated aqueous NaHCO3 (20 mL)
  3. customThe organic layer was separated
  4. dry with materialdried over Na2SO4
  5. customevaporated

출처 및 근거

ORD 기록
ord-cb6dd79796d341109e1d60f3998dfe34
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09040547B2

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