HCID 131728818, compound → HCID 178493032, compound

HRID 592051Notes

Reaction equation

HRID 592051 reaction equation
[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

Participants

3

Reactant 2

HCID 131728818HCID 131728818, compoundHCID 178493031HCID 178493031, compound

Product 1

HCID 178493032HCID 178493032, compoundYield 43.8%

Conditions

Temperature
60 °C

Procedure

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)

Workup

  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

Sources & evidence

ORD record
ord-939c2db05e6a4a3a9a5b9e86dc11b496
Source dataset
uspto-grants-2016_01
Patent number
US09238656B2

Reaction notes

Loading…