Acetic Acid → HCID 59551919, compound

HRID 1170533Notes

Reaction equation

HRID 1170533 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][CH2:11][NH:12][CH2:13][CH2:14][N:15]([C:17]3[S:21][N:20]=[C:19]([N:22]4[CH:26]=[CH:25][N:24]=[CH:23]4)[N:18]=3)[CH3:16])=[CH:9][C:4]=2[O:3][CH2:2]1.[C:27](O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CO>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][CH2:11][N:12]([CH3:27])[CH2:13][CH2:14][N:15]([C:17]3[S:21][N:20]=[C:19]([N:22]4[CH:26]=[CH:25][N:24]=[CH:23]4)[N:18]=3)[CH3:16])=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 59551937HCID 59551937, compound

Product 1

HCID 59551919HCID 59551919, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N′-(2-Benzo[1,3]dioxol-5-yl-ethyl)-N-(3-imidazol-1-yl-[1,2,4]thiadiazol-5-yl)-N-methyl-ethane-1,2-diamine (438 mg, 1.20 mmol) was dissolved in methanol (8 mL) and acetic acid (1.0 mL) and stirred at room temperature for 15 minutes. After this period, the sodium triacetoxyborohydride (750 mg, 3.60 mmol) was added and the reaction was allowed to stir at room temperature After this period, the reaction mixture was concentrated down under vacuum. The crude material was purified by Prep LCMS and the fractions were concentrated down. This material was then neutralized with 1M NaOH and extracted with DCM to afford 303 mg of N-(2-benzo[1,3]dioxol-5-yl-ethyl)-N′-(3-imidazol-1-yl-[1,2,4]thiadiazol-5-yl)-N,N′-dimethyl-ethane-1,2-diamine. [M+H]+ 387.31; 1H NMR (400 MHz, CDCl3) δ 8.26 (s, 1H), 7.62 (s, 1H), 7.05 (s, 1H), 6.66-6.53 (m, 3H), 5.85 (s, 1H), 3.12 (m, 3H), 2.68-2.60 (m, 6H), 2.31 (s, 3H).

Workup

  1. waitAfter this period
  2. concentrationthe reaction mixture was concentrated down under vacuum
  3. customThe crude material was purified by Prep LCMS
  4. concentrationthe fractions were concentrated down
  5. extractionextracted with DCM

Sources & evidence

ORD record
ord-ba9b98ecc6a046b08fc389d3aa307c38
Source dataset
uspto-grants-2010_11
Patent number
US07825256B2

Reaction notes

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