Ammonia → tert-butyl (S)-2-({4-[5-(4-chlorophenyl)pyridin-2-ylethynyl]phenylamino}methyl)pyrrolidine-1-carboxylate

HRID 734865

반응식

HRID 734865 반응식
O.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:18]=[CH:19][C:20]([C:23]#[C:24][C:25]3[CH:30]=[CH:29][C:28](I)=[CH:27][CH:26]=3)=[N:21][CH:22]=2)=[CH:13][CH:12]=1.[NH2:32][CH2:33][C@@H:34]1[CH2:38][CH2:37][CH2:36][N:35]1[C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40].C(N(CC)C(=O)C1C(=CC=CC=1)O)C.N>CN(C=O)C.[Cu]I.CCOC(C)=O>[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:18]=[CH:19][C:20]([C:23]#[C:24][C:25]3[CH:30]=[CH:29][C:28]([NH:32][CH2:33][C@@H:34]4[CH2:38][CH2:37][CH2:36][N:35]4[C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])=[CH:27][CH:26]=3)=[N:21][CH:22]=2)=[CH:13][CH:12]=1

참가 물질

9

반응물 5

HCID 222AmmoniaHCID 88006DiethylsalicylamideHCID 1512533tert-Butyl (2S)-2-(aminomethyl)pyrrolidine-1-carboxylateHCID 22031701Potassium phosphate, tribasic, monohydrateHCID 690599295-(4-Chlorophenyl)-2-(4-iodophenylethynyl)pyridine

생성물 1

HCID 57845306tert-butyl (S)-2-({4-[5-(4-chlorophenyl)pyridin-2-ylethynyl]phenylamino}methyl)pyrrolidine-1-carboxylate

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
100 °C

실험 절차

4.90 g (20.00 mmol) of potassium phosphate monohydrate were added under argon to a mixture of 4.16 g (10.00 mmol) of 5-(4-chlorophenyl)-2-(4-iodophenylethynyl)pyridine, 3.10 g (15.00 mmol) of tert-butyl (S)-2-aminomethylpyrrolidine-1-carboxylate, 194 mg (1.00 mmol) of CuI, 0.77 g (4.00 mmol) of N,N-diethylsalicylamide in 10 mL of DMF and the mixture was stirred for 16 hours at 100° C. The reaction mixture was combined with 100 mL of 5% aqueous ammonia, stirred, and the precipitate was filtered off. The precipitate was purified by MPLC (Hyperprep HS C18, 8 μm, gradient 0.15% formic acid in water/acetonitrile 10/90→90/10 v/v). 2 fractions were isolated. Fraction 1: yield: 0.48 g (10% of theoretical); C29H30ClN3O2 (M=488.020) molpeak (M+H)+: 488/490 (Cl); found: molpeak (M+H)+: 488/490 (Cl); Rf value: 0.60 (silica gel, PE/EtOAc 1:1).

후처리

  1. stirringstirred
  2. filtrationthe precipitate was filtered off
  3. customThe precipitate was purified by MPLC (Hyperprep HS C18, 8 μm, gradient 0.15% formic acid in water/acetonitrile 10/90→90/10 v/v)
  4. custom2 fractions were isolated

출처 및 근거

ORD 기록
ord-dc3cf34d9e2045688d4114cd2f6b3540
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07592358B2

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