Diethyl Ether → HCID 59556692, compound

HRID 1172960Notes

Reaction equation

HRID 1172960 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[N:16]=[C:15]([C:17]3[N:18]=[C:19]4[CH2:24][N:23](C(OCC5C=CC=CC=5)=O)[CH2:22][CH2:21][N:20]4[C:35]=3[CH3:36])[O:14][N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10].C([SiH](C(C)C)C(C)C)(C)C.CCOCC>Br.C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[N:16]=[C:15]([C:17]3[N:18]=[C:19]4[CH2:24][NH:23][CH2:22][CH2:21][N:20]4[C:35]=3[CH3:36])[O:14][N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10]

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 138754Silane, tris(1-methylethyl)-HCID 59556726HCID 59556726, compound

Product 1

HCID 59556692HCID 59556692, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolvent

Procedure

A solution of benzyl 2-(3-(3-chloro-4-isopropoxypheny)-1,2,4-oxadiazol-5-yl)-3-methy-5,6-dihydroimidazo[1,2-a] pyrazine-7(8H)-carboxylate (160 mg, 0.315 mmol) in 33% HBr solution in acetic acid (2.00 mL) containing triisopropylsilane (0.065 mL, 0.315 mmol)) was stirred at room temperature under nitrogen for 10 minutes. Ether (20 ml) was added to precipitate the product. The resulting solid was filtered off, treated with saturated bicarbonate solution (10 ml) and extracted with methylene chloride (2×10 ml). The combined organic layers were dried over sodium sulfate, filtered, concentrated to solids and dried under reduced pressure to yield 2-[3-(3-Chloro -4-isopropoxy-phenyl)-[1,2,4] oxadiazol-5-yl]-3-methyl-5,6,7,8-tetrahydro-imidazo [1,2-a] pyrazine (113 mg, 96%) as an off-white solid. LCMS (Table 1, Method a) Rl=3.14 min, m/z 374.24 (M+H)+; 1H NMR (400 MHz, DMSO-d6) δ 8.01 (d, 1H), 7.97 (d,d, 1H), 7.36 (d, 1H), 4.81 (m, 1H), 4.66 (s, 2H), 3.90 (s, 2H), 3.87 (t, 2H), 3.12 (t, 2H), 2.60 (s, 3H), 1.34 (d, 6H).

Workup

  1. customto precipitate the product
  2. filtrationThe resulting solid was filtered off
  3. additiontreated with saturated bicarbonate solution (10 ml)
  4. extractionextracted with methylene chloride (2×10 ml)
  5. dry with materialThe combined organic layers were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to solids
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-0e290da606a24cf9b90e203b268c071d
Source dataset
uspto-grants-2010_11
Patent number
US07834039B2

Reaction notes

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