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Diisopropylethylamine → HCID 71197908, 화합물

HRID 2415542
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HRID 2415542 반응식
C(N(CC)C(C)C)(C)C.Cl.[C:11]([N:15]1[CH2:19][C@@H:18]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][C:21]=2[F:27])[C@H:17](C(O)=O)[CH2:16]1)([CH3:14])([CH3:13])[CH3:12].Cl.[Cl:32][C:33]1[CH:34]=[CH:35][C:36]([C:44]2[CH2:45][CH2:46][NH:47][CH2:48][CH:49]=2)=[C:37]([CH2:39][C:40]([O:42][CH3:43])=[O:41])[CH:38]=1.F[P-](F)(F)(F)(F)F.N1([O:66][C:67](N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.ON1C2N=CC=CC=2N=N1.C(=O)(O)[O-].[Na+]>CN(C)C=O>[C:11]([N:15]1[CH2:19][C@@H:18]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][C:21]=2[F:27])[C@H:17]([C:67]([N:47]2[CH2:46][CH:45]=[C:44]([C:36]3[CH:35]=[CH:34][C:33]([Cl:32])=[CH:38][C:37]=3[CH2:39][C:40]([O:42][CH3:43])=[O:41])[CH2:49][CH2:48]2)=[O:66])[CH2:16]1)([CH3:12])([CH3:14])[CH3:13]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 6

HCID 81531DiisopropylethylamineHCID 181649HOAtHCID 516892Sodium BicarbonateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67212109(3S,4R)-1-tert-butyl-4-(2,4-difluorophenyl)pyrrolidine-3-carboxylic acid hydrochlorideHCID 86590371
HCID 86590371, 화합물

생성물 1

HCID 71197908HCID 71197908, 화합물

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

N,N-diisopropylethylamine (1.36 mL, 7.80 mmol) was added to a stirred suspension of (3S,4R)-1-tert-butyl-4-(2,4-difluorophenyl)pyrrolidine-3-carboxylic acid (1-7) (0.831 g, 2.60 mmol), methyl [5-chloro-2-(1,2,3,6-tetrahydropyridin-4-yl)phenyl]acetate hydrochloride (1-6) (0.690 g, 2.60 mmol), O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (1.19 g, 3.12 mmol) and 1-hydroxy-7-azabenzotriazole (0.425 g, 3.12 mmol) in N,N-dimethylformamide (5.2 mL) at ambient temperature. After approximately 18 h, the reaction mixture was poured into saturated aqueous sodium bicarbonate and extracted three times with ethyl acetate. The combined organic extracts were washed with water, brine, dried (Na2SO4) and concentrated in vacuo. Purification of the crude residue by flash chromatography on silica gel (gradient elution; 0%-15% methanol (containing 10% v/v ammonium hydroxide)/methylene chloride as eluent) provided 1-8 as a pale yellow oil (m/z (ES) 531 (MH+).

후처리

  1. extractionextracted three times with ethyl acetate
  2. washThe combined organic extracts were washed with water, brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customPurification of the crude residue by flash chromatography on silica gel (gradient elution; 0%-15% methanol (containing 10% v/v ammonium hydroxide)/methylene chloride as eluent)

출처 및 근거

ORD 기록
ord-d907e828abaa47ddb437d0fe469e85ac
출처 데이터셋
uspto-grants-2004_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06818658B2

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