1-Hydroxybenzotriazole → (E)-N-acenaphthen-5-ylmethyl-3-(6-amino-pyridin-3-yl)-N-methyl-acrylamide hydrochloride

HRID 1362245노트

반응식

HRID 1362245 반응식
[CH2:1]1[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[C:6]([CH2:13][NH:14][CH3:15])=[CH:5][CH:4]=[C:3]3[CH2:2]1.[NH2:16][C:17]1[N:22]=[CH:21][C:20](/[CH:23]=[CH:24]/[C:25]([OH:27])=O)=[CH:19][CH:18]=1.C1C=CC2N(O)N=NC=2C=1.C(N(C(C)C)CC)(C)C.CCN=C=NCCCN(C)C.[ClH:58]>CN(C=O)C.O>[ClH:58].[CH2:1]1[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[C:6]([CH2:13][N:14]([CH3:15])[C:25](=[O:27])/[CH:24]=[CH:23]/[C:20]2[CH:21]=[N:22][C:17]([NH2:16])=[CH:18][CH:19]=2)=[CH:5][CH:4]=[C:3]3[CH2:2]1

참가 물질

8

반응물 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10487224(2E)-3-(6-aminopyridin-3-yl)prop-2-enoic acidHCID 669671841-(1,2-Dihydroacenaphthylen-5-yl)-N-methylmethanamine

생성물 1

HCID 66967476(E)-N-acenaphthen-5-ylmethyl-3-(6-amino-pyridin-3-yl)-N-methyl-acrylamide hydrochloride수율 32%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To a solution of acenaphthen-5-ylmethyl-methylamine (216 mg, 1.1 mmol), (E)-3-(6-amino-pyridin-3-yl)acrylic acid (164 mg, 1 mmol), HOBt (148 mg, 1.1 mmol) and diisopropylethylamine (0.8 mL, 4.4 mmol) in DMF (20 mL) was added EDC hydrochloride (210 mg, 1.1 mmol). The mixture was stirred overnight at room temperature. Water (100 mL) was added and the solution stirred for 1 hour. The precipitate was collected by filtration. The yellow solid was preabsorded onto silica gel and purified by column chromatography (95:5 CH2Cl2/MeOH). The residue was dissolved into methylene chloride followed by addition of 1M HCl/ether. The precipitate was collected by filtration to afford (E)-N-acenaphthen-5-ylmethyl-3-(6-amino-pyridin-3-yl)-N-methyl-acrylamide hydrochloride (120 mg, 32%) as a white solid and as a mixture of amide rotomers. 1H NMR (300 MHz, DMSO-d6) δ 8.44-8.28 (m, 3H), 7.84-7.72 (m, 1H), 7.59-7.12 (m, 6H), 7.07-6.92 (m, 1H), 5.15-5.02 (2×s, 2H), 3.35-3.15 (bs, 2H), 3.18 (s, 4H), 3.07-2.90 (2×s, 3H); ESI MS m/z 344 [C22H21N3O+H]+.

후처리

  1. stirringthe solution stirred for 1 hour
  2. filtrationThe precipitate was collected by filtration
  3. custompurified by column chromatography (95:5 CH2Cl2/MeOH)
  4. dissolutionThe residue was dissolved into methylene chloride
  5. additionfollowed by addition of 1M HCl/ether
  6. filtrationThe precipitate was collected by filtration

출처 및 근거

ORD 기록
ord-553cad8ba1304c4a8b4e05d87271668d
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07879872B2

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