1,2-Dichloroethane → HCID 131731924, compound

HRID 529346Notes

Reaction equation

HRID 529346 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[F:15][C:16]([F:37])([F:36])[C:17]([N:19]([C@@H:27]1[CH2:29][C@H:28]1[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH2:20][CH:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1)=[O:18].[CH:38]([C:40]1[CH:45]=[CH:44][C:43]([NH:46][S:47]([CH3:50])(=[O:49])=[O:48])=[CH:42][CH:41]=1)=O.[Cl:51]CCCl>>[ClH:51].[F:37][C:16]([F:15])([F:36])[C:17]([N:19]([CH2:20][CH:21]1[CH2:22][CH2:23][N:24]([CH2:38][C:40]2[CH:41]=[CH:42][C:43]([NH:46][S:47]([CH3:50])(=[O:49])=[O:48])=[CH:44][CH:45]=2)[CH2:25][CH2:26]1)[C@@H:27]1[CH2:29][C@H:28]1[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:18]

Participants

5

Reactant 4

HCID 111,2-DichloroethaneHCID 5049666Sodium triacetoxyborohydride2×HCID 189253554-(Methylsulfonylamino)benzaldehydeHCID 867082342,2,2-trifluoro-N-((1R,2S)-2-phenylcyclopropyl)-N-(piperidin-4-ylmethyl)acetamide

Product 1

HCID 131731924HCID 131731924, compound

Procedure

Added sodium triacetoxyborohydride (180 mg, 0.850 mmol) to a solution of 2,2,2-trifluoro-N-((trans)-2-phenylcyclopropyl)-N-(piperidin-4-ylmethyl)acetamide (185 mg, 0.567 mmol), N-(4-formylphenyl)methanesulfonamide (124 mg, 0.624 mmol) in 1,2-Dichloroethane (DCE) (40 mL). Let stir at RT for 16 hours. Added 100 mg of sodium triacetoxyborohydride and let stir at RT for 16 hours. Concentrated on a rotovap. Added water and extracted with DCM. Combined DCM extracts and washed with brine, dried over MgSO4, filtered and rotovapped off DCM. The residue was purified via Biotage (0% to 100% EtOAc:Hex then 0% to 20% MeOH:DCM 25 g-HP—silica gel column). Obtained 210 mg. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.47 (br. s., H), 1.90 (br. s., 4H), 2.08-2.27 (m, 3H), 2.39 (br. s., 1H), 2.65 (s, 1H), 3.04 (br. s., 4H), 3.23-3.76 (m, 3H), 4.14 (br. s., 2H), 6.99-7.15 (m, 2H), 7.2-7.3 (m 3H), 7.46 (br. s., 23H), 7.63 (br. s., 2H), 9.05 (br. s., 1H), 11.69 (br. s., 1H)

Workup

  1. stirringlet stir at RT for 16 hours
  2. concentrationConcentrated on a rotovap
  3. extractionAdded water and extracted with DCM
  4. washCombined DCM extracts and washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customThe residue was purified via Biotage (0% to 100% EtOAc
  8. customObtained 210 mg

Sources & evidence

ORD record
ord-22ff1d8232c14c61a8be03f31308a9f3
Source dataset
uspto-grants-2016_05
Patent number
US09346840B2

Reaction notes

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