Ethylenediamine → 2-[6-chloro-1-(2-morpholin-4-yl-ethyl)-1H-indazol-3-yl]-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (1-pyridin-3-yl-ethyl)-amide

2-[6-Chloro-1-(2-morpholin-4-yl-ethyl)-1H-indazol-3-yl]-5-(2-trimethylsilanylethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (1-pyridin-3-yl-ethyl)-amide (50 mg, 0.076 mmol) was combined with dichloromethane (1 mL) and trifluoroacetic acid (0.17 ml, 2.27 mmol) was added. After stirring for 2 h, the reaction mixture was concentrated in vacuo. The residue was dissolved in dichloromethane (1 mL) and ethylenediamine (0.15 ml, 2.27 mmol) was added. The reaction mixture was stirred for 20 min then concentrated in vacuo and the residue was triturated with water (2 mL). The precipitate was filtered, washed with water and dried to afford 29 mg (68%) of 2-[6-chloro-1-(2-morpholin-4-yl-ethyl)-1H-indazol-3-yl]-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (1-pyridin-3-yl-ethyl)-amide as a yellow solid. MS: (M+H)+=531; 1H NMR (DMSO-d6) δ: 9.11 (s, 1H), 8.71 (br. s., 1H), 8.43-8.58 (m, 3H), 8.29-8.38 (m, 1H), 8.05 (s, 1H), 7.86 (d, J=7.3 Hz, 1H), 7.36 (br. s., 1H), 7.15 (d, J=8.3 Hz, 1H), 5.35 (t, J=6.9 Hz, 1H), 4.65 (br. s., 2H), 3.50 (br. s., 4H), 3.33 (br. s., 4H), 2.84 (br. s., 2H), 1.68 (d, J=6.3 Hz, 3H).

1. additionwas added
2. concentrationthe reaction mixture was concentrated in vacuo
3. dissolutionThe residue was dissolved in dichloromethane (1 mL)
4. stirringThe reaction mixture was stirred for 20 min
5. concentrationthen concentrated in vacuo
6. customthe residue was triturated with water (2 mL)
7. filtrationThe precipitate was filtered
8. washwashed with water
9. customdried

ORD 기록

ord-e3b74535b5e94ac3ba6c4797019f6ea2

출처 데이터셋

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08658646B2