1,2-Dichloroethane → HCID 59178926, compound

HRID 1947670Notes

Reaction equation

HRID 1947670 reaction equation
O.O[N:3]1C2C=CC=CC=2N=N1.[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][CH:22]([CH:25]2[CH2:30][CH2:29][N:28]([C:31]3[CH:36]=[CH:35][C:34]([CH2:37][C:38](O)=[O:39])=[CH:33][CH:32]=3)[CH2:27][CH2:26]2)[CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13].C(Cl)CCl>N.CO.CN(C=O)C>[C:12]([O:16][C:17]([N:19]1[CH2:20][CH2:21][CH:22]([CH:25]2[CH2:30][CH2:29][N:28]([C:31]3[CH:32]=[CH:33][C:34]([CH2:37][C:38]([NH2:3])=[O:39])=[CH:35][CH:36]=3)[CH2:27][CH2:26]2)[CH2:23][CH2:24]1)=[O:18])([CH3:15])([CH3:14])[CH3:13]

Participants

7

Reactant 3

HCID 111,2-DichloroethaneHCID 27960291-Hydroxybenzotriazole hydrateHCID 59178920HCID 59178920, compound

Product 1

HCID 59178926HCID 59178926, compound

Reagents, catalysts & solvents 3

HCID 222AmmoniaSolventHCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

1-Hydroxybenzotriazole hydrate (53 mg; 0.388 mmol) was dissolved in a solution of ammonia in methanol (5 mL; 7M). The solution was evaporated to a white solid. A solution of {4-[1′-(tert-butoxycarbonyl)-4,4′-bipiperidin-1-yl]phenyl}acetic acid (52 mg; 0.129 mmol) in DMF (2 mL) was added, followed by EDC (75 mg; 0.388 mmol). The mixture was stirred at ambient temperature for 1 hr. The reaction was partitioned between iPrOAc (50 mL) and aq. sodium bicarbonate (10 mL). The organic was washed twice more with water (2×10 mL). The organic was dried over magnesium sulfate, filtered and evaporated to a solid. The solid was chromatographed (PTLC; 40:1 CH2Cl2/MeOH), affording the title compound.

Workup

  1. customThe solution was evaporated to a white solid
  2. customThe reaction was partitioned between iPrOAc (50 mL) and aq. sodium bicarbonate (10 mL)
  3. washThe organic was washed twice more with water (2×10 mL)
  4. dry with materialThe organic was dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated to a solid
  7. customThe solid was chromatographed (PTLC; 40:1 CH2Cl2/MeOH)

Sources & evidence

ORD record
ord-5c89f6f0d6244dbc81df7b3142485f15
Source dataset
uspto-grants-2013_03
Patent number
US08399485B2

Reaction notes

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