HCID 131728818, 화합물 → HCID 178480117, 화합물

HRID 592050노트

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HRID 592050 반응식
[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

참가 물질

3

반응물 2

HCID 131728818HCID 131728818, 화합물HCID 178480118HCID 178480118, 화합물

생성물 1

HCID 178480117HCID 178480117, 화합물수율 46%

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온도
60 °C

실험 절차

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)

후처리

  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

출처 및 근거

ORD 기록
ord-a19805f212db443798e45206f60aa03e
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09238656B2

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