Hydrochloric Acid → HCID 57732691, compound

HRID 562305Notes

Reaction equation

HRID 562305 reaction equation
[CH2:1]([S:3]([N:6]1[CH2:11][CH2:10][CH:9]([C:12]2[C:20]3[C:15](=[C:16]([C:31]([NH2:33])=[O:32])[CH:17]=[C:18]([C:21]4[CH:26]=[CH:25][C:24]([CH:27]=[N:28][O:29][CH3:30])=[CH:23][CH:22]=4)[CH:19]=3)[NH:14][CH:13]=2)[CH2:8][CH2:7]1)(=[O:5])=[O:4])[CH3:2].Cl.C([BH3-])#N.[Na+]>C(Cl)Cl.CO.O1CCOCC1>[CH2:1]([S:3]([N:6]1[CH2:7][CH2:8][CH:9]([C:12]2[C:20]3[C:15](=[C:16]([C:31]([NH2:33])=[O:32])[CH:17]=[C:18]([C:21]4[CH:26]=[CH:25][C:24]([CH2:27][NH:28][O:29][CH3:30])=[CH:23][CH:22]=4)[CH:19]=3)[NH:14][CH:13]=2)[CH2:10][CH2:11]1)(=[O:5])=[O:4])[CH3:2]

Participants

7

Reactant 3

HCID 313Hydrochloric Acid3×HCID 5003444Sodium cyanoborohydride2×HCID 86631034HCID 86631034, compound

Product 1

HCID 57732691HCID 57732691, compoundYield 70.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent3×

Conditions

Temperature
0 °C

Procedure

To a solution of 3-[1-(ethylsulfonyl)-4-piperidinyl]-5-(4-{[(methyloxy)imino]methyl}phenyl)-1H-indole-7-carboxamide (21.5 mg, 0.046 mmol) in DCM (3.0 mL) and MeOH (3.0 mL) was added drops of HCl in 1,4-dioxane to maintain pH=4 at 0° C. Sodium cyanoborohydride (29 mg, 0.46 mmol) was then added and stirred overnight at room temperature. Additional HCl in 1,4-dioxane was added to maintain pH=4 in addition to sodium cyanoborohydride (45 mg, 0.72 mmol). Reaction mixture then stirred over 48 h. Additional HCl in 1,4-dioxane was added to maintain pH=4 at 0° C. and stirred till room temperature was achieved. Mixture was quenched with H2O. DCM was then added for aqueous work-up and mixture was concentrated. The reside was then take up in DCM and purified on the SCX SPE cartridge to afford 15.2 mg of the title compound (70%).

Workup

  1. temperatureto maintain pH=4
  2. customReaction mixture
  3. stirringthen stirred over 48 h
  4. temperatureto maintain pH=4 at 0° C.
  5. stirringstirred till room temperature
  6. customMixture was quenched with H2O
  7. additionDCM was then added for aqueous work-up and mixture
  8. concentrationwas concentrated
  9. custompurified on the SCX SPE cartridge

Sources & evidence

ORD record
ord-596c06f6093449da835decc26d9e1224
Source dataset
uspto-grants-2011_11
Patent number
US08063071B2

Reaction notes

Loading…