Ammonia → N-(4-(2-aminoethoxy)-3-(1-methyl-1H-pyrazol-5-yl)phenyl)-3-methoxybenzamide

HRID 1425540노트

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HRID 1425540 반응식
Br[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:21])[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=2)=[CH:7][C:6]=1[C:22]1[N:23]([CH3:27])[N:24]=[CH:25][CH:26]=1.[NH3:28]>CO>[NH2:28][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:21])[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=2)=[CH:7][C:6]=1[C:22]1[N:23]([CH3:27])[N:24]=[CH:25][CH:26]=1

참가 물질

4

반응물 2

HCID 222AmmoniaHCID 46833681HCID 46833681, 화합물

생성물 1

HCID 46833678N-(4-(2-aminoethoxy)-3-(1-methyl-1H-pyrazol-5-yl)phenyl)-3-methoxybenzamide수율 53%

시약·촉매·용매 1

HCID 887Methanol용매

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온도
150 °C

실험 절차

A mixture of N-[4-(2-bromo-ethoxy)-3-(2-methyl-2H-pyrazol-3-yl)-phenyl]-3-methoxy-benzamide (0.5000 g, 1.161 mmol) and ammonia (0.2515 g, 11.62 mmol) in 20 mL of methanol were heated to 150° C. for 30 minutes under microwave irradiation in a heavy walled sealed tube. The reaction mixture was concentrated to produce the crude product that was subjected to purification on HPLC. The proper fractions were collected and lyophilized to afford the title compound as a white solid (TFA salt) in 53% yield. LCMS m/z (%)=367 (M+H, 100). 1H NMR (400 MHz, DMSO-d6) δ 10.2 (s, 1H), 7.83 (dd, J=2.53 and J2=8.89 Hz, 1H), 7.68 (d, J1=2.53 Hz, 1H), 7.53 (d, J1=8.08 Hz, 1H), 7.48 (m, 1H), 7.46 (d, 31=1.78 Hz, 1H), 7.43 (d, J1=8.08 Hz, 1H), 7.19-7.13, (m, 2H), 6.27 (d, J1=1.77 Hz, 1H), 3.95 (t, J1=5.80 Hz, 2H), 3.83 (s, 3H), 3.69 (s, 3H), 2.8 (t, J1=5.80 Hz, 2H).

후처리

  1. concentrationThe reaction mixture was concentrated
  2. customto produce the crude product that
  3. customwas subjected to purification on HPLC
  4. customThe proper fractions were collected

출처 및 근거

ORD 기록
ord-8c21dc04ec704798b8bcc3f0bcf30ee4
출처 데이터셋
uspto-grants-2015_01
특허 번호
USRE045336E1

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