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 577678ノート

反応式

HRID 577678 の反応式
[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

参加物

4

反応物 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

生成物 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-carbonitrile収率 99%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-cb6dd79796d341109e1d60f3998dfe34
出典データセット
uspto-grants-2015_05
特許番号
US09040547B2

反応ノート

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