HCID 131728818、化合物 → HCID 178480117、化合物

HRID 592050ノート

反応式

HRID 592050 の反応式
[Cl:1][C:2]1[C:3]([NH:17][C:18]23[C:24]([CH3:26])([CH3:25])[C:21]([CH3:27])([CH2:22][CH2:23]2)[C:20](=[O:28])[CH2:19]3)=[C:4]2[N:10]=[C:9]([C:11]3[CH:12]=[N:13][N:14]([CH3:16])[CH:15]=3)[NH:8][C:5]2=[N:6][CH:7]=1.C(O)C.[BH4-].[Na+]>>[Cl:1][C:2]1[C:3]([NH:17][C@@:18]23[C:24]([CH3:25])([CH3:26])[C:21]([CH3:27])([CH2:22][CH2:23]2)[CH:20]([OH:28])[CH2:19]3)=[C:4]2[N:10]=[C:9]([C:11]3[CH:12]=[N:13][N:14]([CH3:16])[CH:15]=3)[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 178480118HCID 178480118、化合物

生成物 1

HCID 178480117HCID 178480117、化合物収率 46%

反応条件

温度
60 °C

実験手順

To a suspension of 4-(6-chloro-2-(1-methyl-1H-pyrazol-4-yl)-3H-imidazo[4,5-b]pyridin-7-ylamino)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one (Compound CXCIX) (90 mg, 0.228 mmol) in ethanol NaBH4 (85 mg, 2.26 mmol) was added and the reaction mixture was heated at 60° C. for 16 h when LCMS confirmed consumption of staring 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 (42 mg, 46%) as a white solid. NMR: δ (1H, 400M Hz, DMSO-d6): 0.88 (3H, s), 0.91 (3H, s), 1.09 (3H, s), 1.10-1.60 (4H, m), 2.75-2.90 (1H, m), 3.60-3.75 (1H, m), 3.94 (3H, s), 4.77 (1H, d, J=4.4 Hz), 5.21 (1H, s), 7.95 (1H, s), 8.03 (1H, s), 8.28 (1H, s), 12.99 (1H, s). LCMS (254 nm): [M+H]+ 401.05 (96.59%). HPLC: 93.58% (220 nm)

後処理

  1. additionwas added
  2. customconsumption of staring 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-a19805f212db443798e45206f60aa03e
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…