1,2-Dichloroethane → HCID 9894399, 화합물

HRID 1271079노트

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HRID 1271079 반응식
[NH2:1][C@@H:2]1[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:6]2[CH:15]=[CH:16][CH:17]=[CH:18][C:5]=2[N:4]([CH2:19][C:20]([F:23])([F:22])[F:21])[C:3]1=[O:24].[C:25]([C:28]1[CH:29]=[C:30]2[C:35](=[CH:36][CH:37]=1)[CH2:34][C:33]1([C:41](=[O:42])[NH:40][C:39](=[O:43])[NH:38]1)[CH2:32][CH2:31]2)(O)=[O:26].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C(N(CC)C(C)C)(C)C>CN(C=O)C>[O:43]=[C:39]1[NH:38][C:33]2([CH2:32][CH2:31][C:30]3[C:35](=[CH:36][CH:37]=[C:28]([C:25]([NH:1][C@@H:2]4[N:8]=[C:7]([C:9]5[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=5)[C:6]5[CH:15]=[CH:16][CH:17]=[CH:18][C:5]=5[N:4]([CH2:19][C:20]([F:21])([F:23])[F:22])[C:3]4=[O:24])=[O:26])[CH:29]=3)[CH2:34]2)[C:41](=[O:42])[NH:40]1

참가 물질

7

반응물 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 10854086HCID 10854086, 화합물HCID 18440314(+/-)-6'-carboxy-3',4'-dihydro-1'H-spiro[imidazolidine-4,2'-naphthalene]-2,5-dione2회

생성물 1

HCID 9894399HCID 9894399, 화합물

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A mixture of (3R)-3-amino-2-oxo-5-phenyl-1-(2,2,2-trifluoroethyl)-2,3-dihydro-1H-1,4-benzodiazepine (Shi et al. Tetrahedron 1999, 55, 909) (507 mg, 1.52 mmol), (±)-6′-carboxy-3′,4′-dihydro-1′H-spiro[imidazolidine-4,2′-naphthalene]-2,5-dione (described in Intermediate 1) (396 mg, 1.52 mmol), EDC (438 mg, 2.28 mmol), HOBT (308 mg, 2.01 mmol), and N,N-diisopropylethylamine (0.795 mL, 4.56 mmol) was stirred in DMF (5 mL) at ambient temperature for 18 h. The crude mixture was partitioned between saturated aqueous NaHCO3 (25 mL) and CH2Cl2 (25 mL), and the aqueous phase was extracted further with CH2Cl2 (2×25 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated to dryness. The crude product was purified by silica gel chromatography, eluting with a gradient of CH2Cl2:MeOH—100:0 to 95:5 to provide the title compound as an off-white solid. MS: m/z=576 (M+1). HRMS: m/z=576.1840; calculated m/z=576.1853 for C30H24F3N5 O4.

후처리

  1. customThe crude mixture was partitioned between saturated aqueous NaHCO3 (25 mL) and CH2Cl2 (25 mL)
  2. extractionthe aqueous phase was extracted further with CH2Cl2 (2×25 mL)
  3. dry with materialThe combined organic extracts were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. customThe crude product was purified by silica gel chromatography
  7. washeluting with a gradient of CH2Cl2

출처 및 근거

ORD 기록
ord-a537a8565ae54c4284fe537c94006322
출처 데이터셋
uspto-grants-2007_04
특허 번호
US07205293B2

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