Acetic Acid → HCID 46852211, compound

HRID 241670Notes

Reaction equation

HRID 241670 reaction equation
[NH:1]1[CH2:4][CH:3]([S:5]([C:8]2[CH:26]=[CH:25][C:11]3[N:12]([CH2:20][CH2:21][N:22]([CH3:24])[CH3:23])[C:13]([CH2:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[N:14][C:10]=3[CH:9]=2)(=[O:7])=[O:6])[CH2:2]1.[C:27](O)(=O)[CH3:28].C(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl.CO>[CH2:27]([N:1]1[CH2:4][CH:3]([S:5]([C:8]2[CH:26]=[CH:25][C:11]3[N:12]([CH2:20][CH2:21][N:22]([CH3:24])[CH3:23])[C:13]([CH2:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[N:14][C:10]=3[CH:9]=2)(=[O:6])=[O:7])[CH2:2]1)[CH3:28]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 177AcetaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 58513578HCID 58513578, compound

Product 1

HCID 46852211HCID 46852211, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 2-(5-(azetidin-3-ylsulfonyl)-2-neopentyl-1H-benzo[d]imidazol-1-yl)-N,N-dimethylethanamine (STEP A, 25 mg, 0.066 mmol), acetic acid (11 microL, 0.20 mmol) and acetaldehyde (75 microL, 1.3 mmol) in dichloromethane (1 mL) and methanol (0.5 mL) was added sodium triacetoxyborohydride (28 mg, 0.13 mmol) at room temperature. After 1 h, the mixture was concentrated. The residue was diluted with methanol (4 mL). The solution was filtered through SCX column and the column was washed with 1 mol/L ammonia in methanol solution (2 mL×2) to wash out the desired compound. The filtrate was concentrated in vacuo. The residue was purified by prep-LC-MS (“process A”).

Workup

  1. concentrationthe mixture was concentrated
  2. additionThe residue was diluted with methanol (4 mL)
  3. filtrationThe solution was filtered through SCX column
  4. washthe column was washed with 1 mol/L ammonia in methanol solution (2 mL×2)
  5. washto wash out the desired compound
  6. concentrationThe filtrate was concentrated in vacuo
  7. customThe residue was purified by prep-LC-MS (“process A”)

Sources & evidence

ORD record
ord-66965468446847088f942133ed7bc0f0
Source dataset
uspto-grants-2014_02
Patent number
US08653063B2

Reaction notes

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