Trifluoroacetic acid → 2-Amino-1-{5-[4-(benzothiazol-2-yloxy)-benzyl]-hexahydro-pyrrolo[3,4-b]pyrrol-1-yl}-ethanone

HRID 384526노트

반응식

HRID 384526 반응식
Cl.[NH:2]1[CH2:6][CH2:5][CH:4]2[CH2:7][N:8]([CH2:10][C:11]3[CH:26]=[CH:25][C:14]([O:15][C:16]4[S:17][C:18]5[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=5[N:20]=4)=[CH:13][CH:12]=3)[CH2:9][CH:3]12.CCN(CC)CC.C([NH:41][CH2:42][C:43](O)=[O:44])(OC(C)(C)C)=O.Cl.CN(C)CCCN=C=NCC.FC(F)(F)C(O)=O>C(Cl)Cl.CO.CS(C)=O>[NH2:41][CH2:42][C:43]([N:2]1[CH2:6][CH2:5][CH:4]2[CH2:7][N:8]([CH2:10][C:11]3[CH:26]=[CH:25][C:14]([O:15][C:16]4[S:17][C:18]5[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=5[N:20]=4)=[CH:13][CH:12]=3)[CH2:9][CH:3]12)=[O:44]

참가 물질

8

반응물 5

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 78288N-(tert-butoxycarbonyl)glycineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 425990812-[4-(Hexahydro-pyrrolo[3,4-b]pyrrol-5-ylmethyl)-phenoxy]-benzothiazole hydrochloride

생성물 1

HCID 425995902-Amino-1-{5-[4-(benzothiazol-2-yloxy)-benzyl]-hexahydro-pyrrolo[3,4-b]pyrrol-1-yl}-ethanone수율 35%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 22036561Dimethyl sulfoxide methanol용매

실험 절차

To a stirred solution of 2-[4-(hexahydro-pyrrolo[3,4-b]pyrrol-5-ylmethyl)-phenoxy]-benzothiazole hydrochloride (100 mg, 0.26 mmol) and Et3N (215 μL, 1.6 mmol) in CH2Cl2 (2 mL) was added N-Boc-glycine (95 mg, 0.5 mmol), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (104 mg, 0.5 mmol). The resulting solution was then stirred at rt for 16 h. The resulting mixture was then treated with trifluoroacetic acid (1 mL) at rt for 3 h. The crude solid was dissolved in CH3OH/DMSO (2:1) and purified via reverse phase preparative HPLC to yield the title compound as a fluffy white solid (37 mg, 35%). MS (ESI): mass calcd. for C22H24N4O2S, 408.5; m/z found, 409.2 [M+H]+. 1H NMR (500 MHz, CDCl3): 7.74 (d, J=8.1 Hz, 1H), 7.68 (d, J=8.0 Hz, 1H), 7.43-7.33 (m, 3H), 7.33-7.26 (m, 3H), 4.51-4.42 (m, 1H), 4.27-4.19 (m, 0.5H), 4.02-3.92 (m, 0.5H), 3.66 (d, J=13.2 Hz, 1H), 3.58 (d, J=5.0 Hz, 0.5H), 3.51-3.37 (m, 3H), 3.28 (d, J=16.7 Hz, 0.5H), 2.91-2.76 (m, 2H), 2.70-2.60 (m, 1H), 2.58-2.50 (m, 1H), 2.50-2.37 (m, 1H), 2.14-1.96 (m, 1H), 1.97-1.80 (m, 1H).

후처리

  1. custompurified via reverse phase preparative HPLC

출처 및 근거

ORD 기록
ord-ae299868a9154c85b9cf7726cf3662f2
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08367719B2

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