Sodium hydride → Adamantane-1-carboxylic acid[6-methanesulfonyl-3-(2-methoxyethyl)-3H-benzothiazol-2-ylidene]-amide

HRID 255071

Reaction equation

HRID 255071 reaction equation
[CH3:1][S:2]([C:5]1[CH:26]=[CH:25][C:8]2[N:9]=[C:10]([NH:12][C:13]([C:15]34[CH2:24][CH:19]5[CH2:20][CH:21]([CH2:23][CH:17]([CH2:18]5)[CH2:16]3)[CH2:22]4)=[O:14])[S:11][C:7]=2[CH:6]=1)(=[O:4])=[O:3].[H-].[Na+].[CH3:29][O:30][CH2:31][CH2:32]Br>>[CH3:1][S:2]([C:5]1[CH:26]=[CH:25][C:8]2[N:9]([CH2:32][CH2:31][O:30][CH3:29])[C:10](=[N:12][C:13]([C:15]34[CH2:22][CH:21]5[CH2:20][CH:19]([CH2:18][CH:17]([CH2:23]5)[CH2:16]3)[CH2:24]4)=[O:14])[S:11][C:7]=2[CH:6]=1)(=[O:3])=[O:4]

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 809722-Bromoethyl methyl etherHCID 5000635Adamantane-1-carboxylic acid (6-methanesulfonyl-benzothiazol-2-yl)-amide

Product 1

HCID 24890596Adamantane-1-carboxylic acid[6-methanesulfonyl-3-(2-methoxyethyl)-3H-benzothiazol-2-ylidene]-amide

Procedure

The product from Example 62A, sodium hydride (60% solution in mineral oil) and 2-bromoethyl methyl ether were processed as described for Example 17B to afford the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.61-1.80 (m, 6 H), 1.87-1.94 (m, 6 H), 1.99-2.07 (m, 3 H), 3.24 (s, 3 H), 3.26 (s, 3 H), 3.78 (t, J=5.4 Hz, 2 H), 4.63 (t, J=5.3 Hz, 2 H), 7.82-7.91 (m, 1 H), 7.93-8.03 (m, 1 H), 8.46 (d, J=1.7 Hz, 1 H); MS (ESI+) m/z 449 (M+H)+; Anal. Calculated for C22H28N2O4S2: C, 58.90; H, 6.29; N, 6.24. Found: C, 58.86; H, 6.30; N, 6.25.

Sources & evidence

ORD record
ord-3d91c08ce048401989942e24aebd016e
Source dataset
uspto-grants-2011_01
Patent number
US07875639B2

Linked notes

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