HCID 24949378, compound → HCID 24949228, compound

HRID 877402Notes

Reaction equation

HRID 877402 reaction equation
[C:1]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][C:9]([C:11]2[O:12][C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18](Br)[N:17]=3)=[N:14][N:15]=2)=[O:10])=[CH:3][CH:2]=1.C1(CCCCCCC(C2OC(C3N=C([C:54]([O:56][CH3:57])=[O:55])C=CC=3)=NN=2)=O)C=CC=CC=1>CO.C(Cl)Cl>[C:1]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][C:9]([C:11]2[O:12][C:13]([C:16]3[N:17]=[C:18]([C:54]([O:56][CH3:57])=[O:55])[CH:19]=[CH:20][CH:21]=3)=[N:14][N:15]=2)=[O:10])=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 24949378HCID 24949378, compoundHCID 24950843HCID 24950843, compound

Product 1

HCID 24949228HCID 24949228, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

The title compound was prepared from 30 (70 mg, 0.16 mmol) by using a procedure similar to that detailed for 8f. Flash chromatography (SiO2, 2.5×15 cm, 0-1% MeOH—CH2Cl2) afforded the title compound (32 mg, 48%) as a white solid: 1H NMR (CDCl3, 600 MHz) δ 8.47 (d, 1H, J=7.8 Hz), 8.34 (d, 1H, J=7.8 Hz), 8.10 (t, 1H, J=7.8 Hz), 7.57 (d, 2H, J=7.2 Hz), 7.53 (d, 2H, J=8.1 Hz), 7.43 (t, 2H, J=7.7 Hz), 7.33 (m, 3H), 4.06 (s, 3H), 3.61 (t, 2H, J=7.5 Hz), 3.19 (t, 2H, J=7.5 Hz); 13C NMR (CDCl3, 150 MHz) δ 186.1, 164.9, 164.6, 161.5, 149.3, 142.9, 141.0, 139.7, 138.9, 138.8, 129.0, 128.9, 127.9, 127.5, 127.3, 127.2, 127.1, 53.4, 41.8, 29.1; HRMS-ESI-TOF m/z 414.1451 ([M+H]+, C24H19N3O4 requires 414.1448).

Sources & evidence

ORD record
ord-206f8bd3c2e44101b278147e5c4890ff
Source dataset
uspto-grants-2015_03
Patent number
US08987312B2

Reaction notes

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