Diisopropylethylamine → HCID 178494839, 화합물

HRID 541321노트

반응식

HRID 541321 반응식
[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]

참가 물질

8

반응물 5

HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 193916184-(Piperidin-4-yl)benzonitrile--hydrogen chloride (1/1)2회HCID 178494842HCID 178494842, 화합물2회

생성물 1

HCID 178494839HCID 178494839, 화합물

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-5a2bdc7da98a46f48321d0335fe79844
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08871790B2

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