4-N-Boc-4-N-Methyl-aminopiperidine → HCID 57551838, compound

HRID 907311Notes

Reaction equation

HRID 907311 reaction equation
[CH:1]1([NH:4][C:5](=[O:31])[C:6]2[CH:11]=[C:10]([F:12])[C:9]([CH3:13])=[C:8]([C:14]3[CH:15]=[C:16]4[C:21](=[CH:22][CH:23]=3)[C:20](=[O:24])[N:19]([CH2:25][CH:26]3[CH2:28][CH2:27]3)[CH:18]=[C:17]4[CH:29]=O)[CH:7]=2)[CH2:3][CH2:2]1.[CH3:32][N:33]([CH:41]1[CH2:46][CH2:45][NH:44][CH2:43][CH2:42]1)C(=O)OC(C)(C)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[CH:1]1([NH:4][C:5](=[O:31])[C:6]2[CH:11]=[C:10]([F:12])[C:9]([CH3:13])=[C:8]([C:14]3[CH:15]=[C:16]4[C:21](=[CH:22][CH:23]=3)[C:20](=[O:24])[N:19]([CH2:25][CH:26]3[CH2:27][CH2:28]3)[CH:18]=[C:17]4[CH2:29][N:44]3[CH2:45][CH2:46][CH:41]([NH:33][CH3:32])[CH2:42][CH2:43]3)[CH:7]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 27568064-N-Boc-4-N-Methyl-aminopiperidineHCID 5049666Sodium triacetoxyborohydrideHCID 57551841N-Cyclopropyl-3-(2-(cyclopropylmethyl)-4-formyl-1-oxo-1,2-dihydroisoquinolin-6-yl)-5-fluoro-4-methylbenzamide

Product 1

HCID 57551838HCID 57551838, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of the product of Example 75 step i) (320 mg) in dichloromethane (15 mL) was added methylpiperidine-4-yl-carbamic acid, tert-butyl ester (490 mg) and the reaction was stirred at room temperature for 10 minutes before the addition of sodium triacetoxyborohydride (490 mg). The reaction was then stirred at room temperature for 24 hours. The reaction mixture was diluted with dichloromethane (50 mL), washed with water (50 mL), dried over magnesium sulfate, filtered and evaporated in vacuo. The residue was then dissolved in methanol (5 mL) and treated with hydrogen chloride (4N in 1,4-dioxane, 10 mL) and stirred at room temperature for 1 hour. The reaction mixture was evaporated in vacuo and the residue was purified (SiO2, chromatography eluting with 5% methanol in dichloromethane to 5% 7N ammonia/methanol in dichloromethane) to afford the title compound as a solid (250 mg).

Workup

  1. washwashed with water (50 mL)
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. dissolutionThe residue was then dissolved in methanol (5 mL)
  6. additiontreated with hydrogen chloride (4N in 1,4-dioxane, 10 mL)
  7. stirringstirred at room temperature for 1 hour
  8. customThe reaction mixture was evaporated in vacuo
  9. customthe residue was purified
  10. wash(SiO2, chromatography eluting with 5% methanol in dichloromethane to 5% 7N ammonia/methanol in dichloromethane)

Sources & evidence

ORD record
ord-91231b123ce149c9bdb7e8ce51062bb3
Source dataset
uspto-grants-2011_09
Patent number
US08012979B2

Reaction notes

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