(S)-(+)-Methyl glycidyl ether → HCID 86615980, compound

HRID 1190171Notes

Reaction equation

HRID 1190171 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[NH:12][CH:13]=[C:14]([C:16]#[N:17])[N:15]=2)=[O:10])=[C:4]([C:18]2[CH2:23][CH2:22][C:21]([CH3:25])([CH3:24])[CH2:20][CH:19]=2)[CH:3]=1.[CH3:26][O:27][CH2:28][C@H:29]1[O:31][CH2:30]1>>[CH3:24][C:21]1([CH3:25])[CH2:22][CH2:23][C:18]([C:4]2[CH:3]=[C:2]([CH2:30][C@@H:29]([OH:31])[CH2:28][O:27][CH3:26])[CH:7]=[CH:6][C:5]=2[NH:8][C:9]([C:11]2[NH:15][C:14]([C:16]#[N:17])=[CH:13][N:12]=2)=[O:10])=[CH:19][CH2:20]1

Participants

3

Reactant 2

HCID 6992187(S)-(+)-Methyl glycidyl etherHCID 1784244434-Cyano-1H-imidazole-2-carboxylic acid [4-bromo-2-(4,4-dimethyl-cyclohex-1-enyl)-phenyl]-amide

Product 1

HCID 86615980HCID 86615980, compound

Procedure

This compound was prepared from 4-cyano-1H-imidazole-2-carboxylic acid [4-bromo-2-(4,4-dimethyl-cyclohex-1-enyl)-phenyl]-amide (as prepared in Example 14, step (c)) according to the procedure in Example 46 step (a) using (S)-glycidyl methyl ether as the electrophile. 1H-NMR (400 MHz, CD3OD): δ 8.10 (d, J=8.3 Hz, 1H), 7.98 (s, 1H), 7.15 (dd, J=8.3, 2.1 Hz, 1H), 7.07 (d, J=2.1 Hz, 1H), 5.73 (m, 1H), 3.91 (m, 1H), 3.36 (s, 3H), 2.80 (dd, J=13.7, 5.7 Hz, 1H), 2.69 (dd, J=13.7, 7.5 Hz, 1H), 2.31 (m, 2H), 2.07 (m, 2H), 1.58 (t, J=6.3 Hz, 2H), 1.07 (s, 6H). Mass spectrum (ESI, m/z): Calcd. for C23H28N4O3, 409.2 (M+H). found 409.1.

Sources & evidence

ORD record
ord-6ed1bba7df3c4f6dac83615503eacf14
Source dataset
uspto-grants-2014_03
Patent number
US08674100B2

Reaction notes

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