1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 16660980, 화합물

HRID 2097152노트

반응식

HRID 2097152 반응식
[F:1][C:2]1[CH:14]=[CH:13][C:5]2[S:6][C:7]([CH2:10][NH:11][CH3:12])=[C:8]([CH3:9])[C:4]=2[CH:3]=1.[O:15]=[C:16]1[NH:25][C:24]2[N:23]=[CH:22][C:21](/[CH:26]=[CH:27]/[C:28]([OH:30])=O)=[CH:20][C:19]=2[CH2:18][CH2:17]1.ON1C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.CN(C)CCCN=C=NCC>CN(C=O)C.O>[F:1][C:2]1[CH:14]=[CH:13][C:5]2[S:6][C:7]([CH2:10][N:11]([CH3:12])[C:28](=[O:30])/[CH:27]=[CH:26]/[C:21]3[CH:22]=[N:23][C:24]4[NH:25][C:16](=[O:15])[CH2:17][CH2:18][C:19]=4[CH:20]=3)=[C:8]([CH3:9])[C:4]=2[CH:3]=1

참가 물질

8

반응물 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 11746081HCID 11746081, 화합물HCID 59456918(5-fluoro-3-methylbenzo[b]thiophen-2-yl)-N-methylmethanamine

생성물 1

HCID 16660980HCID 16660980, 화합물수율 75%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To a solution of (5-fluoro-3-methylbenzo[b]thiophen-2-yl)-N-methylmethanamine (168 mg, 0.8 mmol) in DMF (5 mL) were added in sequential order (E)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylic acid (159 mg, 0.73 mmol), 1-hydroxybenzotriazole (111 mg, 0.8 mmol), diisopropylethylamine (381 uL, 2.19 mmol), and N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide (160 mg, 0.8 mmol). The mixture was stirred at room temperature overnight, cooled in an ice bath and water added with rapid stirring. The product precipitated and was filtered, triturated with ether and dried to yield the title compound as a pale brown solid (224 mg, 75%): 1H NMR (300 MHz, DMSO-d6) δ 10.65 (s, 1H), 8.37 (s, 1H), 8.08 (s, 1H), 7.76-8.00 (m, 1H), 7.39-7.63 (m, 2H), 7.02-7.33 (m, 2H), 4.87-5.11 (rotamers, 2s, 2H), 3.16 (s, 3H), 2.56-2.89 (m, 2H), 2.49-2.51 (m, 2H), 2.39 (s, 3H); MS (ESI) m/e 410 (C22H20FN3O2S+H)+.

후처리

  1. temperaturecooled in an ice bath
  2. customThe product precipitated
  3. filtrationwas filtered
  4. customtriturated with ether
  5. customdried

출처 및 근거

ORD 기록
ord-eca618792fa24508891ede653d7bfc5b
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08450307B2

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