Diisopropylethylamine → HCID 59553169, 화합물

HRID 1641290노트

반응식

HRID 1641290 반응식
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][CH2:13][C:14]#[N:15])=[CH:4][CH:3]=1.[F:16][C:17]1[CH:18]=[C:19]([CH:23]=[C:24]([N:26]2[CH2:31][CH2:30][CH:29]([CH3:32])[CH2:28][CH2:27]2)[CH:25]=1)[C:20](O)=[O:21].C(N(C(C)C)CC)(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C)C=O.C(OCC)(=O)C>[C:14]([CH2:13][O:12][C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]([NH:1][C:20](=[O:21])[C:19]2[CH:23]=[C:24]([N:26]3[CH2:27][CH2:28][CH:29]([CH3:32])[CH2:30][CH2:31]3)[CH:25]=[C:17]([F:16])[CH:18]=2)=[CH:3][CH:4]=1)#[N:15]

참가 물질

7

반응물 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59553077(4-Aminonaphthalen-1-yloxy)-acetonitrileHCID 595533113-Fluoro-5-(4-methylpiperidin-1-yl)benzoic acid

생성물 1

HCID 59553169HCID 59553169, 화합물수율 18.1%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

(4-Aminonaphthalen-1-yloxy)-acetonitrile (1.068 g, 5.4 mmol), 3-fluoro-5-(4-methylpiperidin-1-yl)-benzoic acid (1.27 g, 5 4 mmol), diisopropylethylamine (3 ml) and HBTU (2.45 g, 6.5 mmol) are stirred at room temperature in anhydrous dimethylformamide (20 ml) for 1 day. The mixture is then poured into ethyl acetate (200 ml) and washed with water (2×200 ml). The organic layer is then dried over anhydrous sodium sulfate and evaporated to dryness. The residue is purified by column chromatography on silica gel eluted with 25-30% ethyl acetate in hexanes to give a pale purple solid. This is then recrystalized from ethyl acetate/methanol to give N-(4-cyanomethoxynaphthalen-1-yl)-3-fluoro-5-(4-methylpiperidin-1-yl)-benzamide as a pale purple solid (303 mg). 1H NMR 300 MHz (CDCl3) 8.27(d, 1H, J=7.5 Hz), 7.94(s, 1H), 7.86(t, 2H, J=9.6 Hz), 7.6(m, 2H), 7.3(s, 1H), 6.97(m, 2H), 6.77(d, 1H, J=11.4 Hz), 5.0(s, 1H), 3.77(m, 2H), 2.83(m, 2H), 1.75(m, 2H), 1.25-1.4(m, 3H), 1.0(d, 3H).

후처리

  1. washwashed with water (2×200 ml)
  2. dry with materialThe organic layer is then dried over anhydrous sodium sulfate
  3. customevaporated to dryness
  4. customThe residue is purified by column chromatography on silica gel
  5. washeluted with 25-30% ethyl acetate in hexanes
  6. customto give a pale purple solid
  7. customThis is then recrystalized from ethyl acetate/methanol

출처 및 근거

ORD 기록
ord-dbf128f90647442ab867bb92ef262de0
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08114873B2

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