Hydrochloric Acid → HCID 118308082, 화합물

HRID 1750461

반응식

HRID 1750461 반응식
[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

참가 물질

9

반응물 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

생성물 1

HCID 118308082HCID 118308082, 화합물

시약·촉매·용매 2

HCID 887Methanol용매HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-6e020f263d164325bcfa26555829af99
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09156829B2

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