Diisopropylethylamine → HCID 178494839、化合物

HRID 541321ノート

反応式

HRID 541321 の反応式
[CH:1]([C:4]1[C:12]([C:13]2[NH:17][C:16]([CH2:18][CH2:19][O:20][CH3:21])=[N:15][N:14]=2)=[CH:11][C:7]([C:8]([OH:10])=O)=[C:6]([CH3:22])[CH:5]=1)([CH3:3])[CH3:2].Cl.[NH:24]1[CH2:29][CH2:28][CH:27]([C:30]2[CH:37]=[CH:36][C:33]([C:34]#[N:35])=[CH:32][CH:31]=2)[CH2:26][CH2:25]1.O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.CCN(C(C)C)C(C)C>C(OCC)(=O)C.CN(C=O)C>[CH:1]([C:4]1[C:12]([C:13]2[NH:17][C:16]([CH2:18][CH2:19][O:20][CH3:21])=[N:15][N:14]=2)=[CH:11][C:7]([C:8]([N:24]2[CH2:29][CH2:28][CH:27]([C:30]3[CH:37]=[CH:36][C:33]([C:34]#[N:35])=[CH:32][CH:31]=3)[CH2:26][CH2:25]2)=[O:10])=[C:6]([CH3:22])[CH:5]=1)([CH3:2])[CH3:3]

参加物

8

反応物 5

HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 193916184-(Piperidin-4-yl)benzonitrile--hydrogen chloride (1/1)2 回HCID 178494842HCID 178494842、化合物2 回

生成物 1

HCID 178494839HCID 178494839、化合物

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a 4-mL vial was added 4-Isopropyl-5-(5-(2-methoxyethyl)-4H-1,2,4-triazol-3-yl)-2-methylbenzoic acid (compound 198.6, 31 mg, 0.10 mmol, 1.0 equiv), 4-(piperidin-4-yl)benzonitrile hydrochloride (compound 1.5, 23 mg, 0.10 mmol, 1.0 equiv), 1-hydroxybenzotriazole hydrate (20 wt % water) (22 mg, 0.13 mmol, 1.25 equiv), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (21.5 mg, 0.11 mmol, 1.1 equiv), DMF (1 mL) and DIEA (71 μL, 0.41 mmol, 4 equiv). The mixture was stirred at room temperature for 24 hours then diluted with ethyl acetate (10 mL) and washed with brine (10 mL). The aqueous was back extracted with ethyl acetate (3 mL) and the combined organics was washed with saturated NaHCO3 (5 mL), 1 M NaH2PO4 (5 mL), and brine (5 mL). The organics were dried (Na2SO4), filtered and removed in vacuo. The crude residue was purified by preparative TLC (DCM/8% MeOH) to obtain the title compound as an off white solid (23 mg, 48%). m/z (ES+) 472 (M+H)+.

後処理

  1. washwashed with brine (10 mL)
  2. extractionThe aqueous was back extracted with ethyl acetate (3 mL)
  3. washthe combined organics was washed with saturated NaHCO3 (5 mL), 1 M NaH2PO4 (5 mL), and brine (5 mL)
  4. dry with materialThe organics were dried (Na2SO4)
  5. filtrationfiltered
  6. customremoved in vacuo
  7. customThe crude residue was purified by preparative TLC (DCM/8% MeOH)

出典と根拠

ORDレコード
ord-5a2bdc7da98a46f48321d0335fe79844
出典データセット
uspto-grants-2014_10
特許番号
US08871790B2

反応ノート

読み込み中…