N-(2,4-dimethoxybenzyl)thiazol-2-amine → N-(2,4-dimethoxybenzyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-N-(thiazol-2-yl)naphthalene-2-sulfonamide

HRID 1473346Notes

Reaction equation

HRID 1473346 reaction equation
[CH3:1][O:2][C:3]1[CH:37]=[C:36]([O:38][CH3:39])[CH:35]=[CH:34][C:4]=1[CH2:5][N:6]([C:29]1[S:33]N=[CH:31][N:30]=1)[S:7]([C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][C:16]=2[B:20]2[O:24][C:23]([CH3:26])([CH3:25])[C:22]([CH3:28])([CH3:27])[O:21]2)[CH:11]=1)(=[O:9])=[O:8].[CH3:40]OC1C=C(OC)C=CC=1CNC1SC=CN=1.COC1C=C(OC)C=CC=1CNC1SN=CN=1>>[CH3:1][O:2][C:3]1[CH:37]=[C:36]([O:38][CH3:39])[CH:35]=[CH:34][C:4]=1[CH2:5][N:6]([C:29]1[S:33][CH:40]=[CH:31][N:30]=1)[S:7]([C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][C:16]=2[B:20]2[O:21][C:22]([CH3:27])([CH3:28])[C:23]([CH3:26])([CH3:25])[O:24]2)[CH:11]=1)(=[O:8])=[O:9]

Participants

4

Reactant 3

HCID 49931979N-(2,4-dimethoxybenzyl)thiazol-2-amineHCID 57732216N-(2,4-dimethoxybenzyl)-1,2,4-thiadiazol-5-amineHCID 86687343N-(2,4-dimethoxybenzyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-N-(1,2,4-thiadiazol-5-yl)naphthalene-2 sulfonamide

Product 1

HCID 86687396N-(2,4-dimethoxybenzyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-N-(thiazol-2-yl)naphthalene-2-sulfonamide

Procedure

Intermediate II was synthesized in a similar manner to Intermediate E, using N-(2,4-dimethoxybenzyl)thiazol-2-amine instead of N-(2,4-dimethoxybenzyl)-1,2,4-thiadiazol-5-amine (Intermediate A) in Step 3, to yield N-(2,4-dimethoxybenzyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-N-(thiazol-2-yl)naphthalene-2-sulfonamide as a white solid. m/z (ESI) 567.3 (M+H)+.

Sources & evidence

ORD record
ord-90e52f2725524b818e4833b8e6acd868
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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