Diisopropylethylamine → N-(1-Methyl-5-methyloxycarbonylpyrrol-3-yl)-5-[(1,2-dihydro-1,2-dioxonaphth-4-yl)oxy]valeramide

HRID 1179502노트

반응식

HRID 1179502 반응식
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=O)=[CH:4][C:3]1=[O:20].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.Cl.[NH2:55][C:56]1[CH:60]=[C:59]([C:61]([O:63][CH3:64])=[O:62])[N:58]([CH3:65])[CH:57]=1>CN(C=O)C.CCOCC>[CH3:65][N:58]1[C:59]([C:61]([O:63][CH3:64])=[O:62])=[CH:60][C:56]([NH:55][C:17](=[O:19])[CH2:16][CH2:15][CH2:14][CH2:13][O:12][C:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:2](=[O:1])[C:3](=[O:20])[CH:4]=2)=[CH:57]1

참가 물질

7

반응물 4

HCID 81531Diisopropylethylamine2회HCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 2794656methyl 4-amino-1-methyl-1H-pyrrole-2-carboxylate hydrochlorideHCID 226478225-[(1,2-Dioxo-1,2-dihydronaphth-4-yl)oxy]valeric Acid

생성물 1

HCID 22647811N-(1-Methyl-5-methyloxycarbonylpyrrol-3-yl)-5-[(1,2-dihydro-1,2-dioxonaphth-4-yl)oxy]valeramide수율 40%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매

실험 절차

A solution of an acid 503 (334 mg, 1.22 mmol) in DMF (1.67 mL) was treated with HBTU (462 mg, 1.22 mmol) followed by DIEA (452 mg, 3.5 mmol) and stirred for 5 min. 3-Amino-1-methyl-5-methyloxycarbonylpyrrol hydrochloride (232 mg, 1.22 mmol) and DIEA (378 mg, 3 mmol) were added to the reaction mixture. The latter was stirred for 2 h, diluted with Et2O, the precipitate was removed, dissolved in CHCl3, washed with 3% HCl, H2O, aqueous NaHCO3, H2O again, dried (MgSO4) and purified by chromatography on alumina column (CHCl3/MeOH 80:1, 50:1). The product was triturated with Et2O/CHCl3 to obtain a yellow-red solid (200 mg, 40%); mp 122-123° C. (decomp.): MS (LSIMS, 3-NBA) 410 (M+), 237 (M+−173). 1H NMR (CDCl3) 8.08 (d, J=7.5 Hz, 1H), 7.86 (d, J=7.3 Hz, 1H), 7.68 (t, J=7.5 Hz, 1H), 7.57 (t, J=7.5 Hz, 1H), 7.38 (d, J=1.8 Hz, 1H), 7.34 (s, 1H), 6.65 (d, J=2 Hz, 1H), 5.95 (s, 1H), 4.19 (t, J=5.53 Hz, 2H), 3.88 (s, 3H), 3.80 (s, 3H), 2.46 (t, J=6.6 Hz, 2H), 1.90-2.15 (m, 4H).

후처리

  1. stirringThe latter was stirred for 2 h
  2. customthe precipitate was removed
  3. dissolutiondissolved in CHCl3
  4. washwashed with 3% HCl, H2O, aqueous NaHCO3, H2O again
  5. dry with materialdried (MgSO4)
  6. custompurified by chromatography on alumina column (CHCl3/MeOH 80:1, 50:1)
  7. customThe product was triturated with Et2O/CHCl3

출처 및 근거

ORD 기록
ord-c2657263100a4c0891a7691f1f9d7f7a
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07279502B2

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