Triethylamine → N-[1-(4-biphenylyl)-2-(4-morpholinyl)ethyl]-2-(6,7-dichloro-3-oxo-2,3-dihydro-4H-1,4-benzoxazin-4-yl)-N-methylacetamide

HRID 2354377노트

반응식

HRID 2354377 반응식
[C:1]1([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:6]=[CH:5][C:4]([CH:7]([NH:15][CH3:16])[CH2:8][N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)=[CH:3][CH:2]=1.[Cl:23][C:24]1[C:25]([Cl:38])=[CH:26][C:27]2[O:32][CH2:31][CH2:30][N:29]([CH2:33][C:34]([OH:36])=O)[C:28]=2[CH:37]=1.CN([P+]([O:49]N1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>CN(C=O)C>[C:1]1([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:2]=[CH:3][C:4]([CH:7]([N:15]([CH3:16])[C:34](=[O:36])[CH2:33][N:29]2[C:28]3[CH:37]=[C:24]([Cl:23])[C:25]([Cl:38])=[CH:26][C:27]=3[O:32][CH2:31][C:30]2=[O:49])[CH2:8][N:9]2[CH2:10][CH2:11][O:12][CH2:13][CH2:14]2)=[CH:5][CH:6]=1

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 57418663HCID 57418663, 화합물HCID 57425536[1-(4-Biphenylyl)-2-(4-morpholinyl)ethyl]methylamine

생성물 1

HCID 44561196N-[1-(4-biphenylyl)-2-(4-morpholinyl)ethyl]-2-(6,7-dichloro-3-oxo-2,3-dihydro-4H-1,4-benzoxazin-4-yl)-N-methylacetamide수율 59.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of [1-(4-biphenylyl)-2-(4-morpholinyl)ethyl]methylamine (3.67 g, 12.4 mmol) and (6,7-dichloro-2,3-dihydro-4H-1,4-benzoxazin-4-yl)acetic acid (3.42 g, 12.4 mmol) in DMF (50 mL) was added BOP Reagent (8.23 g, 18.6 mmol) followed by triethylamine (3.76 g, 37.2 mmol). The resultant mixture was stirred at room temperature for 16 h. The mixture was concentrated under reduced pressure, diluted with ethyl acetate (150 mL), and extracted with 5% NaHCO3 (100 mL) and brine (100 mL). The organic layer was dried (MgSO4) and concentrated. The residue was purified by silica gel chromatography (330 g redisep column, silica 40 um, 60 A, 100 ml/min, A: MeOH, B: CH2Cl2, A: 1% for 30 min) to give 4.08 g (59%) of title compound as a white solid. MS (ES) m/e 554.4 [M+H]+.

후처리

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additiondiluted with ethyl acetate (150 mL)
  3. extractionextracted with 5% NaHCO3 (100 mL) and brine (100 mL)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography (330 g redisep column, silica 40 um, 60 A, 100 ml/min

출처 및 근거

ORD 기록
ord-760edc8c264f42c1a83954c04dc0cb6c
출처 데이터셋
uspto-grants-2010_07
특허 번호
US07749998B2

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