1,2-Dichloroethane → HCID 178432867, 화합물

HRID 1875068노트

반응식

HRID 1875068 반응식
C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[NH2:15][CH2:16][C:17]1[C:18]([F:34])=[C:19]([O:24][C:25]2[CH:26]=[C:27]([CH:30]=[C:31]([Cl:33])[CH:32]=2)[C:28]#[N:29])[C:20]([Br:23])=[CH:21][CH:22]=1.[Cl:35][C:36]1[N:37]=[C:38]([CH3:44])[NH:39][C:40]=1[C:41](O)=[O:42]>CN(C=O)C>[Br:23][C:20]1[CH:21]=[CH:22][C:17]([CH2:16][NH:15][C:41]([C:40]2[NH:39][C:38]([CH3:44])=[N:37][C:36]=2[Cl:35])=[O:42])=[C:18]([F:34])[C:19]=1[O:24][C:25]1[CH:26]=[C:27]([C:28]#[N:29])[CH:30]=[C:31]([Cl:33])[CH:32]=1

참가 물질

6

반응물 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 671971663-{[3-(Aminomethyl)-6-bromo-2-fluorophenyl]oxy}-5-chlorobenzonitrileHCID 178432882HCID 178432882, 화합물

생성물 1

HCID 178432867HCID 178432867, 화합물수율 12.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

EDC (0.060 g, 0.311 mmol) and HOBT (0.042 g, 0.311 mmol) were added to a solution of 3-{[3-(aminomethyl)-6-bromo-2-fluorophenyl]oxy}-5-chlorobenzonitrile (0.111 g, 0.311 mmol) and 4-chloro-2-methyl-1H-imidazole-5-carboxylic acid (0.050 g, 0.311 mmol) in DMF (2 mL). The mixture was stirred at RT overnight. The reaction mixture was extracted with EtOAc and saturated sodium bicarbonate and the organic layer was dried over sodium sulfate and concentrated. Rerverse phase HPLC (acetonitrile:water with 0.1% formic acid) gave the title compound (0.019 g, 12%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.86 (br. s., 1H), 8.17 (br. s., 1H), 7.77-7.88 (m, 1H), 7.57-7.66 (m, 1H), 7.46-7.55 (m, 1H), 7.44 (br. s., 1H), 7.22-7.35 (m, 1H), 4.37-4.70 (m, 2H), 2.28 (s, 3H). LCMS: m/z 497, 499.

후처리

  1. extractionThe reaction mixture was extracted with EtOAc and saturated sodium bicarbonate
  2. dry with materialthe organic layer was dried over sodium sulfate
  3. concentrationconcentrated

출처 및 근거

ORD 기록
ord-d611fc9608b34b1b99cab5caec5b2f16
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08304419B2

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