Acetic Acid → HCID 90418427, compound

HRID 633581Notes

Reaction equation

HRID 633581 reaction equation
[F:1][C:2]1[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:3]=1[O:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=O)=[CH:7][C:6]=1[C:13]1[C:21]2[C:16](=[C:17]([O:22][CH3:23])[N:18]=[CH:19][CH:20]=2)[N:15]([CH3:24])[CH:14]=1.C([BH3-])#N.[Na+].[N:34]1([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]1.C(O)(=O)C>CO.ClCCl>[F:1][C:2]1[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:3]=1[O:4][C:5]1[CH:12]=[CH:11][C:8]([CH2:9][N:37]2[CH2:38][CH2:39][N:34]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:35][CH2:36]2)=[CH:7][C:6]=1[C:13]1[C:21]2[C:16](=[C:17]([O:22][CH3:23])[N:18]=[CH:19][CH:20]=2)[N:15]([CH3:24])[CH:14]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 143452tert-Butyl piperazine-1-carboxylateHCID 5003444Sodium cyanoborohydrideHCID 90417507HCID 90417507, compound

Product 1

HCID 90418427HCID 90418427, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
75 °C

Procedure

A suspension of Example 105B (100 mg, 0.254 mmol), sodium cyanoborohydride (47.8 mg, 0.761 mmol) and tert-butyl piperazine-1-carboxylate (94 mg, 0.51 mmol) in a mixture of methanol (3 mL), acetic acid (0.073 mL, 1.3 mmol), and dichloromethane (1 mL) was heated at 75° C. 2 hours. Upon cooling, the reaction mixture was partitioned between 50% saturated sodium bicarbonate solution (50 mL) and ethyl acetate (50 mL). The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified by flash column chromatography (silica gel, 0-3% methanol in dichloromethane) to provide the title compound (66.7 mg, 47% yield).

Workup

  1. custom2 hours
  2. temperatureUpon cooling
  3. customthe reaction mixture was partitioned between 50% saturated sodium bicarbonate solution (50 mL) and ethyl acetate (50 mL)
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash column chromatography (silica gel, 0-3% methanol in dichloromethane)

Sources & evidence

ORD record
ord-984d2f45210b4b76a4f08689698a73a5
Source dataset
uspto-grants-2016_04
Patent number
US09321764B2

Reaction notes

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