HCID 131728818、化合物 → HCID 178493032、化合物

HRID 592051ノート

反応式

HRID 592051 の反応式
[Cl:1][C:2]1[C:3]([NH:25][C:26]23[C:32]([CH3:34])([CH3:33])[C:29]([CH3:35])([CH2:30][CH2:31]2)[C:28](=[O:36])[CH2:27]3)=[C:4]2[N:10]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([N:17]4[CH2:22][CH2:21][O:20][CH2:19][CH2:18]4)=[CH:13][C:12]=3[O:23][CH3:24])[NH:8][C:5]2=[N:6][CH:7]=1.C(O)C.[BH4-].[Na+]>>[Cl:1][C:2]1[C:3]([NH:25][C:26]23[C:32]([CH3:33])([CH3:34])[C:29]([CH3:35])([CH2:30][CH2:31]2)[CH:28]([OH:36])[CH2:27]3)=[C:4]2[N:10]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([N:17]4[CH2:22][CH2:21][O:20][CH2:19][CH2:18]4)=[CH:13][C:12]=3[O:23][CH3:24])[NH:8][C:5]2=[N:6][CH:7]=1

参加物

3

反応物 2

HCID 131728818HCID 131728818、化合物HCID 178493031HCID 178493031、化合物

生成物 1

HCID 178493032HCID 178493032、化合物収率 43.8%

反応条件

温度
60 °C

実験手順

To a suspension of 4-(6-chloro-2-(2-methoxy-4-morpholinophenyl)-3H-imidazo[4,5-b]pyridin-7-ylamino)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one (Compound CC) (100 mg, 0.196 mmol) in ethanol NaBH4 (74 mg, 1.96 mmol) was added and the reaction mixture was heated at 60° C. for 16 h when LCMS confirmed consumption of starting material and formation of desired product. The reaction mixture was allowed to come to rt and acidified to pH 5. Solvent was then removed and the residue was suspended in water and filtered. The residue was triturated with ether to afford the desired product (44 mg, 43%) as a light green solid. NMR: δ (1H, 400M Hz, DMSO-d6): 0.89 (3H, s), 0.91 (3H, s), 1.09 (3H, s), 1.00-1.60 (4H, m), 2.70-2.90 (1H, m), 3.20-3.30 (4H, m), 3.60-3.70 (1H, m), 3.70-3.80 (4H, m), 3.97 (3H, s), 5.35 (1H, s), 6.54 (1H, s), 6.74 (1H, d, J=8.8 Hz), 8.03 (2H, d, J=8.8 Hz), 12.26 (1H, s). LCMS (254 nm): [M+H]+ 512.15 (91.18%). HPLC: (254 nm) 89.96% (220 nm)

後処理

  1. additionwas added
  2. customconsumption of starting material and formation of desired product
  3. customto come to rt
  4. customSolvent was then removed
  5. filtrationfiltered
  6. customThe residue was triturated with ether

出典と根拠

ORDレコード
ord-939c2db05e6a4a3a9a5b9e86dc11b496
出典データセット
uspto-grants-2016_01
特許番号
US09238656B2

反応ノート

読み込み中…