1,1'-Carbonyldiimidazole → HCID 59471686, 화합물

HRID 78558

반응식

HRID 78558 반응식
[NH:1]1[CH2:5][CH2:4][CH2:3][C@@H:2]1[CH2:6][N:7]1[CH2:11][CH2:10][CH2:9][CH2:8]1.[NH2:12][C:13]1[N:14]=[CH:15][C:16]([C:28]2[CH:29]=[C:30]([CH:34]=[CH:35][CH:36]=2)C(O)=O)=[N:17][C:18]=1[C:19](=[O:27])[NH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C1N=CN([C:42](N2C=NC=C2)=[O:43])C=1.CCN(C(C)C)C(C)C>CN(C1C=CN=CC=1)C.CS(C)=O>[NH2:12][C:13]1[C:18]([C:19]([NH:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[O:27])=[N:17][C:16]([C:28]2[CH:36]=[CH:35][C:34]([C:42]([N:1]3[CH2:5][CH2:4][CH2:3][C@@H:2]3[CH2:6][N:7]3[CH2:11][CH2:10][CH2:9][CH2:8]3)=[O:43])=[CH:30][CH:29]=2)=[CH:15][N:14]=1

참가 물질

7

반응물 4

HCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 853151(R)-(-)-1-(2-Pyrrolidinylmethyl)pyrrolidineHCID 468337433-(5-Amino-6-(phenylcarbamoyl)pyrazin-2-yl)benzoic acid

생성물 1

HCID 59471686HCID 59471686, 화합물수율 73.5%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
38 °C

실험 절차

1-[[(2R)-pyrrolidin-2-yl]methyl]pyrrolidine (69.23 mg, 0.449 mmol) was weighed into a greenhouse tube and treated with a solution of 3-(5-amino-6-(phenylcarbamoyl)pyrazin-2-yl)benzoic acid (50 mg, 0.150 mmol), CDI (48.51 mg, 0.299 mmol) and DMAP (1.82 mg, 0.015 mmol) in DMSO (1 mL of a stock solution). DIPEA (78.2 uL, 0.449 mmol) was then added and the mixture stirred at 38° C. for 6 hours. The reaction mixture was filtered and the resultant residue was purified by reverse phase preparative HPLC [Waters Sunfire C18, 10 uM, 100 A column, gradient 10%-95% B (solvent A: 0.05% TFA in water, solvent B: CH3CN) over 16 minutes at 25 mL/min]. The fractions were freeze-dried to give the title compound as a solid (51.87 mg, 73% Yield).

후처리

  1. filtrationThe reaction mixture was filtered
  2. customthe resultant residue was purified by reverse phase preparative HPLC [Waters Sunfire C18, 10 uM, 100 A column, gradient 10%-95% B (solvent A: 0.05% TFA in water, solvent B: CH3CN) over 16 minutes at 25 mL/min]
  3. customThe fractions were freeze-dried

출처 및 근거

ORD 기록
ord-e41d59218ed049c59525f2f1bd958d5d
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841308B2

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