1-(diphenylmethyl)-1H-indole-2,3-dione → 3-hydroxy-3-(6-hydroxy-4-methyl-3,4-dihydro-2H-1,4-benzoxazin-7-yl)-1-[(2R)-tetrahydrofuran-2-ylmethyl]-1,3-dihydro-2H-indol-2-one

HRID 2385015노트

반응식

HRID 2385015 반응식
[CH3:1][N:2]1[CH2:7][CH2:6][O:5][C:4]2[CH:8]=[CH:9][C:10]([OH:12])=[CH:11][C:3]1=2.O1C2C(=CC=C(O)C=2)CCC1.[O:24]1[CH2:28][CH2:27][CH2:26][C@@H:25]1[CH2:29][N:30]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:32](=[O:39])[C:31]1=[O:40].C1(C(C2C=CC=CC=2)N2C3C(=CC=CC=3)C(=O)C2=O)C=CC=CC=1>>[OH:39][C:32]1([C:9]2[C:10]([OH:12])=[CH:11][C:3]3[N:2]([CH3:1])[CH2:7][CH2:6][O:5][C:4]=3[CH:8]=2)[C:33]2[C:38](=[CH:37][CH:36]=[CH:35][CH:34]=2)[N:30]([CH2:29][C@H:25]2[CH2:26][CH2:27][CH2:28][O:24]2)[C:31]1=[O:40]

참가 물질

5

반응물 4

HCID 19692771-(diphenylmethyl)-1H-indole-2,3-dioneHCID 12236542Chroman-7-olHCID 220305304-methyl-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-olHCID 67358326(R)-1-((tetrahydrofuran-2-yl)methyl)indoline-2,3-dione

생성물 1

HCID 685987153-hydroxy-3-(6-hydroxy-4-methyl-3,4-dihydro-2H-1,4-benzoxazin-7-yl)-1-[(2R)-tetrahydrofuran-2-ylmethyl]-1,3-dihydro-2H-indol-2-one

실험 절차

Following the procedure as described in PREPARATION 14A, and making non-critical variations using 4-methyl-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-ol (McMurtrey, K. D., et al., J. Org. Chem. (1970), 35(12):4252-3) to replace chroman-7-ol, and 1-[(2R)-tetrahydrofuran-2-ylmethyl]-1H-indole-2,3-dione to replace 1-(diphenylmethyl)indoline-2,3-dione, 3-hydroxy-3-(6-hydroxy-4-methyl-3,4-dihydro-2H-1,4-benzoxazin-7-yl)-1-[(2R)-tetrahydrofuran-2-ylmethyl]-1,3-dihydro-2H-indol-2-one was obtained (92%) as a pale brown solid: 1H NMR (300 MHz, CDCl3) δ9.21 (d, J=13.6 Hz, 1H), 7.46 (d, J=7.2 Hz, 1H), 7.36 (dd, J=7.8, 7.8 Hz, 1H), 7.17 (dd, J=7.5, 7.2 Hz, 1H), 7.09 (d, J=7.8 Hz, 1H), 6.40 (s, 1H), 6.18 (s, 1H), 4.25-4.06 (m, 3H), 3.87-3.63 (m, 4H), 3.27-3.17 (m, 2H), 2.87 (s, 3H), 2.02-1.74 (m, 3H), 1.71-1.57 (m, 2H); 13C NMR (75 MHz, CDCl3) δ179.8, 179.7, 151.54, 151.52, 143.1, 143.0, 138.0, 137.4, 130.12, 130.10, 129.32, 129.29, 126.1, 126.0, 123.8, 114.8, 114.6, 113.1, 113.0, 110.4, 110.3, 103.5, 79.11, 79.06, 76.9, 76.7, 68.32, 68.26, 64.6, 48.9, 44.6, 38.5, 29.3, 29.1, 25.7, 25.6; MS (ES+) m/z 418.9 (M+23).

출처 및 근거

ORD 기록
ord-d792f801d41148cdb1d61d86d295665b
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08263606B2

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