Methanol → HCID 117843669, compound

HRID 2209090Notes

Reaction equation

HRID 2209090 reaction equation
[CH:1]1([N:4]2[C:8]3[C:9]([O:28][C@@H:29]([C@@H:31]4[CH2:35][C:34](=[O:36])[NH:33][CH2:32]4)[CH3:30])=[N:10][C:11]([C:13]4[CH:18]=[C:17]5[NH:19][C:20](=[O:27])[C:21]6([CH2:26][CH2:25][NH:24][CH2:23][CH2:22]6)[C:16]5=[CH:15][CH:14]=4)=[CH:12][C:7]=3[N:6]=[CH:5]2)[CH2:3][CH2:2]1.C(O)(C(F)(F)F)=O.CO.[O:46]1[CH2:49][C:48](=O)[CH2:47]1>C(Cl)Cl>[CH:1]1([N:4]2[C:8]3[C:9]([O:28][C@@H:29]([C@@H:31]4[CH2:35][C:34](=[O:36])[NH:33][CH2:32]4)[CH3:30])=[N:10][C:11]([C:13]4[CH:18]=[C:17]5[NH:19][C:20](=[O:27])[C:21]6([CH2:22][CH2:23][N:24]([CH:48]7[CH2:49][O:46][CH2:47]7)[CH2:25][CH2:26]6)[C:16]5=[CH:15][CH:14]=4)=[CH:12][C:7]=3[N:6]=[CH:5]2)[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 887MethanolHCID 6422Trifluoroacetic acidHCID 150242543-OxetanoneHCID 117843728HCID 117843728, compound

Product 1

HCID 117843669HCID 117843669, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-(3-cyclopropyl-4-((R)-1-((R)-5-oxopyrrolidin-3-yl)ethoxy)-3H-imidazo[4,5-c]pyridin-6-yl)spiro[indoline-3,4′-piperidin]-2-one: 3.78 (TFA salt) (28 mg) in DCM (2 mL) and MeOH (1 mL) was added oxetan-3-one (4.98 mg, 0.069 mmol) and TEA (1 mL) (to neutralize TFA). The mixture was stirred for 45 minutes then followed by addition of Na(CN)BH3 (5.1 mg, 0.081 mmol). Reaction mixture was stirred for 30 minutes. Reaction was done based on LCMS. The solvent was removed and the residue was purified by prep HPLC (MeCN:water gradient, TFA modified) to provide 6-(3-cyclopropyl-4-((R)-1-((R)-5-oxopyrrolidin-3-yl)ethoxy)-3H-imidazo[4,5-c]pyridin-6-yl)-1′-(oxetan-3-yl)spiro[indoline-3,4′-piperidin]-2-one: (3.79) as a TFA salt.

Workup

  1. customReaction mixture
  2. stirringwas stirred for 30 minutes
  3. customReaction
  4. customThe solvent was removed
  5. customthe residue was purified by prep HPLC (MeCN:water gradient, TFA modified)

Sources & evidence

ORD record
ord-e9e82f90b0104063926f767a233ffdac
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

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