2-Benzyl-1,2,5-thiadiazolidine 1,1-dioxide → 2-(5-benzyl-1,1-dioxido-1,2,5-thiadiazolidin-2-yl)-4-methyl-N-(pyridin-3-ylmethyl)-1,3-thiazole-5-carboxamide

HRID 560797

Reaction equation

HRID 560797 reaction equation
C(N1CCNC1=NC#N)C1C=CC=CC=1.[CH2:16]([N:23]1[CH2:27][CH2:26][NH:25][S:24]1(=[O:29])=[O:28])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.Br[C:31]1[S:32][C:33]([C:37]([NH:39][CH2:40][C:41]2[CH:42]=[N:43][CH:44]=[CH:45][CH:46]=2)=[O:38])=[C:34]([CH3:36])[N:35]=1>>[CH2:16]([N:23]1[S:24](=[O:29])(=[O:28])[N:25]([C:31]2[S:32][C:33]([C:37]([NH:39][CH2:40][C:41]3[CH:42]=[N:43][CH:44]=[CH:45][CH:46]=3)=[O:38])=[C:34]([CH3:36])[N:35]=2)[CH2:26][CH2:27]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 3

HCID 103758902-Benzyl-1,2,5-thiadiazolidine 1,1-dioxideHCID 666315502-Bromo-4-methyl-N-(pyridin-3-ylmethyl)thiazole-5-carboxamideHCID 178512076HCID 178512076, compound

Product 1

HCID 594812572-(5-benzyl-1,1-dioxido-1,2,5-thiadiazolidin-2-yl)-4-methyl-N-(pyridin-3-ylmethyl)-1,3-thiazole-5-carboxamideYield 79%

Procedure

Following the procedure as described in Example 27, making variations as required to replace N-(1-benzylimidazolidin-2-ylidene)cyanamide with 2-benzyl-1,2,5-thiadiazolidine 1,1-dioxide to react with 2-bromo-4-methyl-N-(pyridin-3-ylmethyl)thiazole-5-carboxamide, the title compound was obtained as a colorless solid in 79% yield: mp 140-142° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, DMSO-d6) δ 8.68 (t, J=5.8 Hz, 1H), 8.49-8.43 (m, 2H), 7.67 (d, J=7.8 Hz, 1H), 7.39-7.28 (m, 6H), 4.37 (d, J=5.8 Hz, 2H), 4.26 (s, 2H), 3.46 (t, J=6.6 Hz, 2H), 3.99 (t, J=6.6 Hz, 2H), 2.46 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ 161.3, 157.2, 152.9, 149.3, 148.5, 135.6, 135.2, 129.6, 129.0, 128.8, 128.5, 124.0, 119.6, 51.3, 46.0, 44.7, 40.9, 17.5; MS (ES+) m/z 444.3 (M+1).

Sources & evidence

ORD record
ord-1c194ca98b5f46bda5028b5b795c9e79
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Linked notes

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