5-Chloro-o-anisic acid → HCID 178490672, compound

HRID 78525Notes

Reaction equation

HRID 78525 reaction equation
[C:1]([C:5]1[S:9][C:8](=[NH:10])[N:7]([CH2:11][C@@H:12]2[CH2:16][CH2:15][CH2:14][O:13]2)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[Cl:17][C:18]1[CH:19]=[CH:20][C:21]([O:27][CH3:28])=[C:22]([CH:26]=1)[C:23](O)=[O:24]>>[C:1]([C:5]1[S:9]/[C:8](=[N:10]\[C:23](=[O:24])[C:22]2[CH:26]=[C:18]([Cl:17])[CH:19]=[CH:20][C:21]=2[O:27][CH3:28])/[N:7]([CH2:11][C@@H:12]2[CH2:16][CH2:15][CH2:14][O:13]2)[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 769705-Chloro-o-anisic acidHCID 686231055-tert-Butyl-3-[(S)-1-(tetrahydro-furan-2-yl)methyl]-3H-thiazol-2-ylideneamine

Product 1

HCID 178490672HCID 178490672, compound

Procedure

The products from Example 315A and 5-chloro-2-methoxy-benzoic acid were processed using the method described in Example 300 to afford the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 1.35 (s, 9H), 1.62-1.95 (m, 3H), 2.00-2.12 (m, 1H), 3.72-3.87 (m, 2H), 3.90 (s, 3H), 4.18-4.34 (m, 2H), 4.42 (dd, J=12.0, 2.4 Hz, 1H), 6.86 (s, 1H), 6.90 (d, J=8.8 Hz, 1H), 7.32 (dd, J=8.8, 2.7 Hz, 1H), 7.95 (d, J=2.7 Hz, 1H). MS (ESI+) m/z 409 (M+H)+.

Sources & evidence

ORD record
ord-acbcd56a6d02454aac3dd2178ce7cb01
Source dataset
uspto-grants-2014_09
Patent number
US08841334B2

Reaction notes

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