HCID 23434725, compound → HCID 178424499, compound

HRID 1190222Notes

Reaction equation

HRID 1190222 reaction equation
[CH3:1][C:2]1([CH3:29])[CH2:7][CH2:6][C:5]([C:8]2[CH:13]=[C:12]([C:14]([CH3:18])([CH3:17])[CH:15]=O)[CH:11]=[CH:10][C:9]=2[NH:19][C:20]([C:22]2[NH:23][CH:24]=[C:25]([C:27]#[N:28])[N:26]=2)=[O:21])=[CH:4][CH2:3]1.[CH3:30][C:31]1([CH3:39])[O:38][CH:34]2[CH2:35][NH:36][CH2:37][CH:33]2[O:32]1>CO.C(Cl)Cl>[CH3:1][C:2]1([CH3:29])[CH2:7][CH2:6][C:5]([C:8]2[CH:13]=[C:12]([C:14]([CH3:15])([CH3:17])[CH2:18][N:36]3[CH2:37][CH:33]4[O:32][C:31]([CH3:39])([CH3:30])[O:38][CH:34]4[CH2:35]3)[CH:11]=[CH:10][C:9]=2[NH:19][C:20]([C:22]2[NH:23][CH:24]=[C:25]([C:27]#[N:28])[N:26]=2)=[O:21])=[CH:4][CH2:3]1

Participants

4

Reactant 2

HCID 23434725HCID 23434725, compoundHCID 178424502HCID 178424502, compound

Product 1

HCID 178424499HCID 178424499, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

The title compound was prepared by the procedure of Example 138, step (i) using 4-cyano-1H-imidazole-2-carboxylic acid [2-(4,4-dimethyl-cyclohex-1-enyl)-4-(1,1-dimethyl-2-oxo-ethyl)-phenyl]-amide (as prepared in Example 138, step (h), 60.0 mg, 0.154 mmol) and 2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole (Couturier, M. et at, Organic Process Research & Development, 2002, 6, 42-48, 132 mg, 0.924 mmol). Silica gel chromatography (1-3% MeOH/DCM) afforded the title compound (49.3 mg, 63%) as a white solid. 1H-NMR (1:1 CD3OD; 400 MHz): 8.13 (d, 1H, J=8.6 Hz), 7.98 (s, 1H), 7.32 (dd, 1H, J=8.6, 2.3 Hz), 7.21 (d, 1H, J=2.3 Hz), 5.73 (m, 1H), 4.48 (m, 2H), 2.70 (d, 2H, J=11.4 Hz), 2.59 (s, 2H), 2.31 (m, 2H), 2.08 (m, 2H), 1.98-2.04 (m, 2H), 1.59 (t, 2H, J=6.3 Hz), 1.44 (s, 3H), 1.34 (s, 6H), 1.23 (s, 3H), 1.09 (s, 6H). Mass spectrum (ESI, m/z): Calcd. for C30H39N5O3, 518.3 (M+H). found 518.3.

Workup

  1. customThe title compound was prepared by the procedure of Example 138, step (i)

Sources & evidence

ORD record
ord-6cbba6e3d8a74dd4b2e32028acaa1415
Source dataset
uspto-grants-2014_03
Patent number
US08674100B2

Reaction notes

Loading…