HCID 66819097, compound → HCID 66821293, compound

HRID 24023Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:16])[C:5]#[C:6][C:7]1[CH:8]=[CH:9][C:10]2[O:14][CH2:13][CH2:12][C:11]=2[CH:15]=1)[CH3:2].[C:17]([O:21][C:22]([N:24]1[C:33]2[C:28](=[CH:29][CH:30]=[C:31]([CH2:34][CH2:35][O:36][C:37]3[CH:38]=[C:39]4[C:43](=[CH:44][CH:45]=3)[NH:42][CH:41]=[CH:40]4)[N:32]=2)[CH2:27][CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:19])[CH3:18]>>[C:17]([O:21][C:22]([N:24]1[C:33]2[C:28](=[CH:29][CH:30]=[C:31]([CH2:34][CH2:35][O:36][C:37]3[CH:38]=[C:39]4[C:43](=[CH:44][CH:45]=3)[N:42]([C:6]([C:7]3[CH:8]=[CH:9][C:10]5[O:14][CH2:13][CH2:12][C:11]=5[CH:15]=3)=[CH:5][C:4]([O:3][CH2:1][CH3:2])=[O:16])[CH:41]=[CH:40]4)[N:32]=2)[CH2:27][CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:18])[CH3:19]

Participants

Reactant 2

HCID 66819097HCID 66819097, compound

HCID 668210837-[2-(1H-indol-5-yloxy)-ethyl]-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid tert-butyl ester

Product 1

HCID 66821293HCID 66821293, compoundYield 52%

Procedure

The title compound was synthesized from (2,3-dihydro-benzofuran-5-yl)-propynoic acid ethyl ester and 7-[2-(1H-indol-5-yloxy)-ethyl]-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid tert-butyl ester using the procedure described in Example 16, step (c1), in 52% yield as an E/Z mixture. 1H NMR (CDCl3) δ 7.31 (d, 1H, J=7.6 Hz), 7.18-7.01 (m, 4H), 6.94 (dd, 1H, J=3.5, 7.6 Hz), 6.82-6.71 (m, 3H), 6.56-6.48 (m, 1H), 6.10 (s, 0.6H), 6.00 (s, 0.4H), 4.62 (q, 2H, J=8.8 Hz), 4.39-4.35 (m, 2H), 4.13 (q, 0.8H, J=7.1 Hz), 3.98 (q, 1.2H, J=7.1 Hz), 3.76 (t, 2H, J=5.9 Hz), 3.23-3.14 (m, 4H), 2.73 (t, 2H, J=6.64 Hz), 1.95-1.89 (m, 2H), 1.52 (s, 9H), 1.21 (t, 1.2H, J=7.1 Hz), 1.00 (t, 1.8 Hz, J=7.1 Hz).

Sources & evidence

ORD record: ord-4a2f52ee86884d63a657340ff6c14a47
Source dataset: uspto-grants-2005_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06855722B2

Reaction notes

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