Ethyl 3-(2H-1,3-benzodioxol-5-yl)prop-2-ynoate → HCID 66821277, compound

HRID 24027Notes

Reaction equation

HRID 24027 reaction equation
[CH2:1]([O:3][C:4](=[O:16])[C:5]#[C:6][C:7]1[CH:15]=[CH:14][C:10]2[O:11][CH2:12][O:13][C:9]=2[CH:8]=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:15]=[CH:14][C:10]5[O:11][CH2:12][O:13][C:9]=5[CH:8]=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

3

Reactant 2

HCID 11275992Ethyl 3-(2H-1,3-benzodioxol-5-yl)prop-2-ynoateHCID 668210837-[2-(1H-indol-5-yloxy)-ethyl]-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid tert-butyl ester

Product 1

HCID 66821277HCID 66821277, compoundYield 39%

Procedure

The title compound was synthesized from benzo[1,3]dioxol-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 39% yield as an E/Z mixture. 1H NMR (CDCl3) δ 7.32 (d, 1H, J=7.6 Hz), 7.10-7.04 (m, 2H), 7.00-6.90 (m, 2H), 6.85-6.71 (m, 4H), 6.56-6.49 (m, 1H), 6.10 (s, 0.6H), 6.04 (s, 0.4H), 6.03 (s, 0.8H), 6.00 (s, 1.2H), 4.40-4.35 (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), 3.20 (t, 2H, 6.8 Hz), 2.73 (t, 2H, 6.7 Hz), 1.95-1.89 (m, 2H), 1.519 (s, 5.4H), 1.516 (s, 3.6 H), 1.22 (t, 1.2H, J=7.1 Hz), 1.01 (t, 1.8H, J=7.1 Hz). Mass Spectrum (LCMS, ESI) calculated for C30H29N3O5 512.3 (M-Boc +1); found 512.3.

Sources & evidence

ORD record
ord-f5d56864095943d38ef0ebb5f6fb3f1c
Source dataset
uspto-grants-2005_02
Patent number
US06855722B2

Reaction notes

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