Triethylamine → HCID 86706102, 화합물

HRID 2176261노트

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HRID 2176261 반응식
Br[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([C@H:12]([NH:14][C:15]([C@@H:17]3[CH2:22][CH2:21][CH2:20][N:19]([C:23](=[O:35])[C@@H:24]([NH:26][C:27](=[O:34])[C@H:28]([CH:30]4[CH2:33][CH2:32][CH2:31]4)[OH:29])[CH3:25])[NH:18]3)=[O:16])[CH3:13])=[N:9]2)=[CH:4][CH:3]=1.[CH3:36][C:37]([CH3:43])([CH:41]=[CH2:42])[C:38]([OH:40])=[O:39].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)CC)C>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].[Pd].[Pd].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1>[CH:30]1([C@H:28]([OH:29])[C:27]([NH:26][C@@H:24]([CH3:25])[C:23]([N:19]2[CH2:20][CH2:21][CH2:22][C@@H:17]([C:15]([NH:14][C@@H:12]([C:8]3[CH:7]=[CH:6][C:5]4[C:10](=[CH:11][C:2](/[CH:42]=[CH:41]/[C:37]([CH3:43])([CH3:36])[C:38]([OH:40])=[O:39])=[CH:3][CH:4]=4)[N:9]=3)[CH3:13])=[O:16])[NH:18]2)=[O:35])=[O:34])[CH2:33][CH2:32][CH2:31]1

참가 물질

8

반응물 4

HCID 8471TriethylamineHCID 80271Tri-o-tolylphosphine2회HCID 1391222,2-Dimethyl-3-butenoic acidHCID 86706103HCID 86706103, 화합물

생성물 1

HCID 86706102HCID 86706102, 화합물

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 9832798Tris(dibenzylideneacetone) dipalladium촉매HCID 312751,4-Dioxane용매

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온도
50 °C

실험 절차

A solution of (S)-1-[(S)-2-((S)-2-cyclobutyl-2-hydroxy-acetylamino)-propionyl]-hexahydro-pyridazine-3-carboxylic acid [(R)-1-(7-bromo-quinolin-2-yl)-ethyl]-amide (427.5 mg, 0.782 mmol), 2,2-dimethyl-but-3-enoic acid (89.3 mg, 0.782 mmol), tri(o-tolyl)phosphine (47.6 mg, 0.156 mmol) and triethylamine (0.33 mL, 2.346 mmol) in 1,4-dioxane (10 mL) was degassed by bubbling nitrogen through for 5 minutes then warmed to 50° C. and treated with tris(dibenzylideneacetone)dipalladium(0) (71.6 mg, 0.078 mmol). After stirring at 100° C. for 1.5 h, tris(dibenzylideneacetone) dipalladium(0) (71.6 mg, 0.078 mmol) and tri(o-tolyl)phosphine (47.6 mg, 0.156 mmol) were added. After stirring for 40 minutes at 100° C., the reaction was cooled to room temperature, filtered through a pad of Celite, which was rinsed with ethyl acetate. The volatiles were removed in vacuo to provide crude title compound as an orange foam that was used without further purification. LCMS (m/z) 580.2 [M+H], Tr=2.01 min.

후처리

  1. customby bubbling nitrogen through for 5 minutes
  2. stirringAfter stirring for 40 minutes at 100° C.
  3. temperaturethe reaction was cooled to room temperature
  4. filtrationfiltered through a pad of Celite, which
  5. washwas rinsed with ethyl acetate
  6. customThe volatiles were removed in vacuo

출처 및 근거

ORD 기록
ord-3a3ca54c7ed64da89f3297267a20ede0
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09062092B2

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