Hydrochloric Acid → HCID 118308082, compound

HRID 1750461

Reaction equation

HRID 1750461 reaction equation
[CH3:1][C:2]1[N:6]=[C:5]([C:7]2[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=2[C:9]([OH:11])=O)[O:4][N:3]=1.[NH2:16][C@H:17]1[CH2:21][CH2:20][CH2:19][C@@H:18]1[NH:22]C(=O)OC(C)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.[ClH:61].O1CCOCC1>CN(C=O)C.CO>[ClH:61].[NH2:16][C@H:17]1[CH2:21][CH2:20][CH2:19][C@@H:18]1[NH:22][C:9](=[O:11])[C:8]1[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=1[C:5]1[O:4][N:3]=[C:2]([CH3:1])[N:6]=1

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 312751,4-DioxaneHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 17040218(1S,2S)-trans-N-Boc-1,2-cyclopentanediamineHCID 231463052-(3-Methyl-1,2,4-oxadiazol-5-yl)benzoic acid

Product 1

HCID 118308082HCID 118308082, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-(3-methyl-1,2,4-oxadiazol-5-yl)benzoic acid (CAS number 475105-77-2; 0.84 g, 4.12 mmol), tert-butyl N-[(1S,2S)-2-aminocyclopentyl]carbamate (CAS number 586961-34-4; 0.75 g, 3.74 mmol), HATU (2.14 g, 5.62 mmol) and triethylamine (1.57 ml, 11.23 mmol) was stirred in dry DMF (12.5 ml) at room temperature for 17 hours. The reaction mixture was partitioned between ethyl acetate and water, washed with water and brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The crude material was then purified by column chromatography (silica, 0-100% ethyl acetate/petrol). The resulting cream solid was recrystalised from ethyl acetate, to which was then added methanol (10 ml) and HCl in 1,4-dioxane (4M, 4.68 ml, 18.72 mmol) and the reaction was stirred at room temperature for 17 hours. The reaction was concentrated in vacuo and azeotropically distilled with toluene to afford the title compound.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. washwashed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude material was then purified by column chromatography (silica, 0-100% ethyl acetate/petrol)
  7. customThe resulting cream solid was recrystalised from ethyl acetate, to which
  8. concentrationThe reaction was concentrated in vacuo
  9. distillationazeotropically distilled with toluene

Sources & evidence

ORD record
ord-6e020f263d164325bcfa26555829af99
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Linked notes

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