HCID 131728818, compound → HCID 178480117, compound

HRID 592050Notes

Reaction equation

HRID 592050 reaction equation
[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

Participants

3

Reactant 2

HCID 131728818HCID 131728818, compoundHCID 178480118HCID 178480118, compound

Product 1

HCID 178480117HCID 178480117, compoundYield 46%

Conditions

Temperature
60 °C

Procedure

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)

Workup

  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

Sources & evidence

ORD record
ord-a19805f212db443798e45206f60aa03e
Source dataset
uspto-grants-2016_01
Patent number
US09238656B2

Reaction notes

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