2-Bromoacetamide → 2-{3-[2-(2-Isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulen-9-yl]-azetidin-1-yl}-acetamide

HRID 708122Notes

Reaction equation

HRID 708122 reaction equation
C(N1C(C2SC3CCOC4C=C(C5CN([CH2:27][C:28]([NH2:30])=[O:29])C5)C=CC=4C=3N=2)=NC=N1)(C)C.[NH:31]1[CH2:34][CH:33]([C:35]2[CH:36]=[CH:37][C:38]3[O:47][CH2:46][CH2:45][C:44]4[S:43][C:42]([C:48]5[N:49]([CH:53]([CH3:55])[CH3:54])[N:50]=[CH:51][N:52]=5)=[N:41][C:40]=4[C:39]=3[CH:56]=2)[CH2:32]1.BrCC(N)=O>CN(C=O)C>[CH:53]([N:49]1[C:48]([C:42]2[S:43][C:44]3[CH2:45][CH2:46][O:47][C:38]4[CH:37]=[CH:36][C:35]([CH:33]5[CH2:34][N:31]([CH2:27][C:28]([NH2:30])=[O:29])[CH2:32]5)=[CH:56][C:39]=4[C:40]=3[N:41]=2)=[N:52][CH:51]=[N:50]1)([CH3:54])[CH3:55]

Participants

5

Reactant 3

HCID 696322-BromoacetamideHCID 582042442-{3-[2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulen-8-yl]-azetidin-1-yl}-acetamideHCID 670505299-azetidin-3-yl-2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene

Product 1

HCID 582040302-{3-[2-(2-Isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulen-9-yl]-azetidin-1-yl}-acetamideYield 53%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Following the procedure of 319, 9-azetidin-3-yl-2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene and bromoacetamide were reacted in DMF to give 371 (111 mg, 53%). LCMS: RT=6.96 min, [M+H]+=425. 1H NMR δ (ppm) (CDCl3): 8.31 (1H, d, J=2.35 Hz), 7.90 (1H, s), 7.17 (1H, dd, J=8.28, 2.36 Hz), 7.03 (1H, d, J=8.26 Hz), 7.01-6.85 (1H, m), 5.91-5.83 (1H, m), 5.41 (1H, s), 4.37 (2H, t, J=5.06 Hz), 3.89 (2H, t, J=7.36 Hz), 3.81-3.73 (1H, m), 3.43-3.34 (4H, m), 3.22 (2H, s), 1.63 (6H, d, J=6.65 Hz)

Sources & evidence

ORD record
ord-122b8116b58343fea3ef8ac59447e7ba
Source dataset
uspto-grants-2015_11
Patent number
US09175009B2

Reaction notes

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