Diisopropylethylamine → [4-[2-(4-Azidobenzoylamino)ethylamino]-5-(4-fluorophenylcarbamoyl)pyrimidin-2-ylsulfanyl]acetic acid ethyl ester

HRID 348495

반응식

HRID 348495 반응식
[N:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8](Cl)=[O:9])=[CH:6][CH:5]=1)=[N+:2]=[N-:3].[CH2:13]([O:15][C:16](=[O:39])[CH2:17][S:18][C:19]1[N:24]=[C:23]([NH:25][CH2:26][CH2:27][NH2:28])[C:22]([C:29](=[O:38])[NH:30][C:31]2[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=2)=[CH:21][N:20]=1)[CH3:14].CCN(C(C)C)C(C)C>CN(C=O)C>[CH2:13]([O:15][C:16](=[O:39])[CH2:17][S:18][C:19]1[N:24]=[C:23]([NH:25][CH2:26][CH2:27][NH:28][C:8](=[O:9])[C:7]2[CH:11]=[CH:12][C:4]([N:1]=[N+:2]=[N-:3])=[CH:5][CH:6]=2)[C:22]([C:29](=[O:38])[NH:30][C:31]2[CH:32]=[CH:33][C:34]([F:37])=[CH:35][CH:36]=2)=[CH:21][N:20]=1)[CH3:14]

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 846684-Azidobenzoyl chlorideHCID 69523574[4-(2-Aminoethylamino)-5-(4-fluorophenylcarbamoyl)pyrimidin-2-ylsulfanyl]acetic acid ethyl ester

생성물 1

HCID 86760402[4-[2-(4-Azidobenzoylamino)ethylamino]-5-(4-fluorophenylcarbamoyl)pyrimidin-2-ylsulfanyl]acetic acid ethyl ester수율 16%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

4-Azidobenzoyl chloride (67 mg, 0.37 mmol) was added to a solution of [4-(2-aminoethylamino)-5-(4-fluorophenylcarbamoyl)pyrimidin-2-ylsulfanyl]acetic acid ethyl ester (145 mg, 0.37 mmol) in DMF (2.0 mL). DIPEA (100 μL, 0.55 mmol, 1.5 eq) was then added to the reaction mixture and the acylation was allowed to proceed overnight at ambient temperature. The reaction mixture was concentrated by rotary evaporation and purified using flash chromatography (4 g silica gel, 10 mL/min flow rate) to yield the titled product (31 mg, 16%) as a clear glass. 1H NMR: (d6-DMSO) δ 10.23 (s, 1H), 8.67 (m, 1H), 8.55 (s, 1H), 7.81 (d, 2H), 7.62 (m, 2H), 7.13 (m, 3H), 4.07 (q, 2H), 3.97 (s, 2H), 3.60 (m, 2H), 3.42 (m, 2H), 1.14 (t, 3H); HPLC: Rt=4.36 min; MS (ESI): m/z 537.31 (M−H)−; IR (KBr): 2126 cm−1.

후처리

  1. concentrationThe reaction mixture was concentrated by rotary evaporation
  2. custompurified

출처 및 근거

ORD 기록
ord-6fb6f6e1f2614eae8b5381bfc11065e8
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07176310B1

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