(4-Amino-3-sulfamoyl-phenyl)-carbamic acid tert-butyl ester → HCID 136347364, 화합물

HRID 601386노트

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HRID 601386 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:4][C:3]=1[S:16]([NH2:19])(=[O:18])=[O:17].CS[C:22](SC)=[C:23]1[C:32](=[O:33])[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[N:25]([NH:34][CH2:35][CH:36]2[CH2:38][CH2:37]2)[C:24]1=[O:39]>O1CCOCC1>[CH:36]1([CH2:35][NH:34][N:25]2[C:26]3[C:31](=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:32]([OH:33])=[C:23]([C:22]3[NH:1][C:2]4[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:13])([CH3:14])[CH3:12])=[CH:4][C:3]=4[S:16](=[O:17])(=[O:18])[N:19]=3)[C:24]2=[O:39])[CH2:37][CH2:38]1

참가 물질

4

반응물 2

HCID 59805694(4-Amino-3-sulfamoyl-phenyl)-carbamic acid tert-butyl esterHCID 670636773-[bis(methylthio)methylene]-1-[(cyclopropylmethyl)amino]quinoline-2,4(1H,3H)-dione

생성물 1

HCID 136347364HCID 136347364, 화합물수율 51%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

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온도
25 °C

실험 절차

A mixture of the product of Example 414A (78.1 mg, 0.272 mmol) and the product of Example 353B (91.0 mg, 0.272 mmol) in anhydrous dioxane (2.7 mL) was heated under reflux for 3 h. The reaction mixture was then cooled to 25° C. and concentrated under reduced pressure to yield an oily solid. The solid was triturated with methanol to yield the title compound (72.5 mg, 51%). 1H NMR (300 MHz, DMSO-d6) δ 0.14 (d, J=4.04 Hz, 2 H) 0.42 (m, 2 H) 1.00 (m, 1 H) 1.51 (s, 9 H) 2.85 (bd, J=4.78 Hz, 2 H) 6.45 (bs, 1 H) 7.44 (t, J=7.54 Hz, 1 H) 7.62 (d, J=8.82 Hz, 1 H) 7.69 (dd, J=8.82, 2.20 Hz, 1 H) 7.89 (m, J=7.91, 7.91 Hz, 1 H) 8.10 (d, J=8.46 Hz, 1 H) 8.17 (m, 2 H) 9.93 (s, 1 H) 14.08 (s, 1 H) 15.15 (d, J=4.78 Hz, 1 H). MS (ESI−) m/z 524.0 (M−H)−. The sodium salt of the compound was prepared by reacting example 414B (3.9 mg, 0.0074 mmol) with 1 N sodium hydroxide solution (0.0074 mL, 0.0074 mmol) in 0.5 mL water and 0.5 mL tetrahydrofuran at room temperature for 1.2 h. The reaction mixture was then evaporated under a stream of nitrogen to provide the sodium salt (4.1 mg, 100% yield). 1H NMR (300 MHz, DMSO-d6) δ 0.20 (m, J=5.52 Hz, 2 H) 0.46 (d, J=8.82 Hz, 2 H) 1.00 (m, 1 H) 1.50 (s, 9 H) 3.30 (m, 2 H) 5.96 (t, J=6.25 Hz, 1 H) 7.06 (t, J=7.17 Hz, 1 H) 7.20 (d, J=9.19 Hz, 1 H) 7.52 (m, 2 H) 7.67 (d, J=8.82 Hz, 1 H) 7.90 (s, 1 H) 8.06 (d, J=7.35 Hz, 1 H) 9.60 (s, 1 H) 16.22 (s, 1 H). MS (ESI+) m/z 543.1 (M+H+H2O-Na)+, 526.1 (M−Na)+, (ESI−) m/z 524.1 (M−H)−.

후처리

  1. temperatureunder reflux for 3 h
  2. concentrationconcentrated under reduced pressure
  3. customto yield an oily solid
  4. customThe solid was triturated with methanol

출처 및 근거

ORD 기록
ord-499985f777e84a24946a9f9c8e9b0c67
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07902203B2

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