N,N-Diethyl-2-propanamine → 4-Methyl-2-pyridin-2-yl-pyrimidine-5-carboxylic acid pyrrol[3,2-b]pyridine-1-ylamide

HRID 2382015

반응식

HRID 2382015 반응식
C(N(CC)C(C)C)C.[CH3:9][C:10]1[C:15]([C:16]([OH:18])=O)=[CH:14][N:13]=[C:12]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)[N:11]=1.[N:25]1([NH2:34])[C:33]2[C:28](=[N:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=[CH:26]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C>[N:25]1([NH:34][C:16]([C:15]2[C:10]([CH3:9])=[N:11][C:12]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=3)=[N:13][CH:14]=2)=[O:18])[C:33]2[C:28](=[N:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=[CH:26]1

참가 물질

6

반응물 4

HCID 521913N,N-Diethyl-2-propanamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 19601545Pyrrolo[3,2-b]pyridin-1-ylamineHCID 617020254-Methyl-2-(pyridin-2-yl)pyrimidine-5-carboxylic acid

생성물 1

HCID 592000594-Methyl-2-pyridin-2-yl-pyrimidine-5-carboxylic acid pyrrol[3,2-b]pyridine-1-ylamide수율 63%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

Diethyl-iso-propylamine (1.88 mmol) is added a solution of 4-methyl-2-pyridin-2-yl-pyrimidine-5-carboxylic acid (0.75 mmol), pyrrolo[3,2-b]pyridine-1-ylamine (0.75 mmol) and TBTU (0.9 mmol) in anhydrous DMF (7 mL) at rt, and the reaction mixture is stirred at 80° C. for 8 h. The reaction mixture is concentrated in vacuo. The residue is purified by silica gel chromatography eluting with 0-10% MeOH in DCM to afford 4-methyl-2-pyridin-2-yl-pyrimidine-5-carboxylic acid pyrrol[3,2-b]pyridine-1-ylamide (155 mg, 63%) as a solid. MS: 331 (M+H); 1H NMR (300 MHz, CD3OD): δ 2.89 (s, 3H), 7.01 (d, H), 7.64-7.77 (m, 2H), 8.15 (m, H), 8.25 (m, H), 8.59-8.76 (m, 3H), 8.82 (d, H), 9.31 (s, 2H). IC50=13 nM.

후처리

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. customThe residue is purified by silica gel chromatography
  3. washeluting with 0-10% MeOH in DCM

출처 및 근거

ORD 기록
ord-ea4e828aed144f28b954f2a476182bed
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08258130B2

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