Dimethylformamide → HCID 86620039, 화합물

HRID 2389511노트

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HRID 2389511 반응식
[C:1]([O:5][C:6](=[O:29])[CH2:7][N:8]1[C:12]2[CH:13]=[CH:14][C:15]([F:17])=[CH:16][C:11]=2[N:10]=[C:9]1[S:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([C:26](O)=[O:27])[CH:21]=1)([CH3:4])([CH3:3])[CH3:2].CCN(CC)CC.C1C=CC2N(O)N=NC=2C=1.Cl.CN(C)CCCN=C=NCC.[NH:59]1[C:67]2[C:62](=[CH:63][CH:64]=[CH:65][CH:66]=2)[CH2:61][CH2:60]1.CN([CH:71]=[O:72])C>>[N:59]1([C:26]([C:22]2[CH:23]=[CH:24][C:25]([O:72][CH3:71])=[C:20]([CH:21]=2)[CH2:19][S:18][C:9]2[N:8]([CH2:7][C:6]([O:5][C:1]([CH3:3])([CH3:4])[CH3:2])=[O:29])[C:12]3[CH:13]=[CH:14][C:15]([F:17])=[CH:16][C:11]=3[N:10]=2)=[O:27])[C:67]2[C:62](=[CH:63][CH:64]=[CH:65][CH:66]=2)[CH2:61][CH2:60]1

참가 물질

7

반응물 6

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 10328IndolineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 131729957HCID 131729957, 화합물

생성물 1

HCID 86620039HCID 86620039, 화합물

실험 절차

To a solution of tert-butyl[2-(3-hydroxycarbonyl-benzylsulfanyl)-5-fluoro-benzoimidazol-1-yl]-acetate (Precursor 5-F-H-00b, 44.6 mg, 0.1 mmol) in dry DMF (0.8 ml) are added successively Et3N (21.1 μl, 15.2 mg, 0.15 mmol, 1.5 eq.), HOBt (23.0 mg, 0.15 mmol, 1.5 eq.), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (28.8 mg, 0.15 mmol, 1.5 eq.) and indoline (16.8 μl, 17.9 mg, 0.15 mmol, 1.5 eq.). The reaction mixture is stirred at rt overnight. The solvents are evaporated under reduced pressure, dichloromethane (4 ml) is added and the resulting organic phase is washed once with 2 ml of a 1 M NaHCO3 solution in water and once with 2 ml of a 1 M solution of sodium hydrogen sulfate in water. The acidic aqueous phase was extracted once with dichloromethane (2 ml). The combined organic phase is washed with brine. The solvent is removed under a stream of air and the resulting crude product is dried under high vacuum overnight yielding the title compound (40 mg) in 83% as a light brown oil: tR=1.20 min (LC-3), ESI-MS (pos.): m/z 548.23 [M+H]+, 1H-NMR (CDCl3): δ (ppm) 1.400 (s, 9H, tBu), 2.95 (t, 2H, NCH2CH2Ar), 3.91 (s, 3H, OCH3), 3.95 (t, 2H, NCH2CH2Ar), 4.65 (s, 2H, SCH2), 4.72 (s, 2H, CH2CO2), 6.91-7.19 (m, 7Harom), 7.45 (m, 1Harom), 7.52 (m, 1Harom), 7.64 (m, 1Harom).

후처리

  1. customThe solvents are evaporated under reduced pressure, dichloromethane (4 ml)
  2. additionis added
  3. washthe resulting organic phase is washed once with 2 ml of a 1 M NaHCO3 solution in water and once with 2 ml of a 1 M solution of sodium hydrogen sulfate in water
  4. extractionThe acidic aqueous phase was extracted once with dichloromethane (2 ml)
  5. washThe combined organic phase is washed with brine
  6. customThe solvent is removed under a stream of air
  7. dry with materialthe resulting crude product is dried under high vacuum overnight

출처 및 근거

ORD 기록
ord-4bac018a9b21426ab937ca3dd20fc1a2
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08273740B2

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