Hydrochloric Acid → HCID 118308082、化合物

HRID 1750461

反応式

HRID 1750461 の反応式
[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

参加物

9

反応物 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

生成物 1

HCID 118308082HCID 118308082、化合物

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-6e020f263d164325bcfa26555829af99
出典データセット
uspto-grants-2015_10
特許番号
US09156829B2

関連ノート

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