Triethylamine → 3-iodo-4-methyl-N-(4-((4-methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)benzamide

HRID 535836노트

반응식

HRID 535836 반응식
[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5](Cl)=[O:6].IC1C=C(C=CC=1C)C(O)=O.O=S(Cl)Cl.[CH3:27][N:28]1[CH2:33][CH2:32][N:31]([CH2:34][C:35]2[CH:41]=[CH:40][C:38]([NH2:39])=[CH:37][C:36]=2[C:42]([F:45])([F:44])[F:43])[CH2:30][CH2:29]1.CCN(CC)CC>CN(C1C=CN=CC=1)C.C1COCC1>[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([NH:39][C:38]1[CH:40]=[CH:41][C:35]([CH2:34][N:31]2[CH2:30][CH2:29][N:28]([CH3:27])[CH2:33][CH2:32]2)=[C:36]([C:42]([F:45])([F:44])[F:43])[CH:37]=1)=[O:6]

참가 물질

8

반응물 5

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 6216403-Iodo-4-methylbenzoic acidHCID 177521573-Iodo-4-methylbenzoyl chlorideHCID 46838908AP-24592

생성물 1

HCID 468389103-iodo-4-methyl-N-(4-((4-methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)benzamide수율 67.2%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 8028Tetrahydrofuran용매

실험 절차

3-Iodo-4-methylbenzoyl chloride (1.06 g, 3.8 mmol), prepared from the reaction of 3-iodo-4-methylbenzoic acid and SOCl2, was added to a solution of 4-((4-methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)aniline (1.00 g, 3.6 mmol), Et3N (0.36 g 3.6 mmol), and a catalytic amount of DMAP in THF (20 mL). After stirring at rt for 2 hrs, the reaction was quenched with water. EtOAc was added and the layers separated. The combined organic layers were concentrated to dryness and purified by silica gel chromatography (eluent: 5% MeOH in CH2Cl2, MeOH was added 0.5% Et3N) to provide the desired product as an off-white solid (67.2%, 1.25 g). 1H NMR (300 MHz, CDCl3) δ: 8.29 (1H, s), 8.00 (1H, s), 7.85 ((1H, m), 7.73-7.76 ((2H, m), 7.31-7.34 ((1H, d, J=9.0 Hz), 3.64 (2H, s), 2.53 (8H, brs), 2.49 (3H, s), 2.33 (3H, s).

후처리

  1. customthe reaction was quenched with water
  2. additionEtOAc was added
  3. customthe layers separated
  4. concentrationThe combined organic layers were concentrated to dryness
  5. custompurified by silica gel chromatography (eluent: 5% MeOH in CH2Cl2, MeOH was added 0.5% Et3N)

출처 및 근거

ORD 기록
ord-48fa6a024c4d424eb41c866372abfdf4
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08859553B2

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