Triethylamine → HCID 57659472, compound

HRID 217199Notes

Reaction equation

HRID 217199 reaction equation
[CH:1]1([OH:5])[CH2:4][CH2:3][CH2:2]1.Cl[C:7](Cl)([O:9]C(=O)OC(Cl)(Cl)Cl)Cl.CCN(CC)CC.[NH:25]1[CH2:30][CH2:29][CH:28]([CH2:31][C:32]2[N:36]=[C:35]([C:37]3[O:45][C:44]4[CH:43]=[CH:42][N:41]=[C:40]([C:46]#[N:47])[C:39]=4[CH:38]=3)[O:34][N:33]=2)[CH2:27][CH2:26]1>C1COCC1.O.C(Cl)Cl>[CH:1]1([O:5][C:7]([N:25]2[CH2:26][CH2:27][CH:28]([CH2:31][C:32]3[N:36]=[C:35]([C:37]4[O:45][C:44]5[CH:43]=[CH:42][N:41]=[C:40]([C:46]#[N:47])[C:39]=5[CH:38]=4)[O:34][N:33]=3)[CH2:29][CH2:30]2)=[O:9])[CH2:4][CH2:3][CH2:2]1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 76218CyclobutanolHCID 94429TriphosgeneHCID 11652480HCID 11652480, compound

Product 1

HCID 57659472HCID 57659472, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of cyclobutyl alcohol (32.6 mg, 452 μmol), triphosgene (44.7 mg, 151 μmol), anhydrous THF (4 mL), and NEt3 (91.6 mg, 905 μmol) was stirred for 30 min. This mixture was added to a stirred solution of 2-(3-piperidin-4-ylmethyl-[1,2,4]oxadiazol-5-yl)furo[3,2-c]pyridine-4-carbonitrile (Preparation 15, 35 mg, 113 μmol) in anhydrous THF (2 mL). After 30 min, the reaction mixture was treated with CH2Cl2 (20 mL) and H2O (10 mL), then, after thorough mixing, the organic layer was separated using a fritted hydrophobic filter. The aqueous phase was extracted with CH2Cl2 (10 mL), the CH2Cl2 layer being isolated by means of a fritted hydrophobic filter. The combined CH2Cl2 solutions were evaporated, then the residue was purified by column chromatography (EtOAc-IH, 1:1) to furnish the title compound: RT=3.84 min; m/z (ES+)=408.1 [M+H]+.

Workup

  1. waitAfter 30 min
  2. customafter thorough mixing, the organic layer was separated
  3. extractionThe aqueous phase was extracted with CH2Cl2 (10 mL)
  4. customthe CH2Cl2 layer being isolated by means of a fritted hydrophobic filter
  5. customThe combined CH2Cl2 solutions were evaporated
  6. customthe residue was purified by column chromatography (EtOAc-IH, 1:1)

Sources & evidence

ORD record
ord-7903a4d6eccc4bc2b6f420ef526d3765
Source dataset
uspto-grants-2012_06
Patent number
US08193359B2

Reaction notes

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