Thioglycolic Acid → HCID 67351119, compound

HRID 1672753Notes

Reaction equation

[C:1]([C:3]1[CH:40]=[CH:39][C:6]([CH2:7][N:8]([CH2:21][C@@H:22]2[CH2:26][CH2:25][CH2:24][N:23]2[C:27]2[C:32]([C:33]([O:35]CC)=S)=[CH:31][N:30]=[C:29](C)[N:28]=2)S(C2C=CC=CC=2[N+]([O-])=O)(=O)=O)=[CH:5][CH:4]=1)#[N:2].[SH:41][CH2:42]C(O)=O.C1CCN2C(=NCCC2)CC1>CN(C=O)C.C(O)C.C(OCC)(=O)C>[C:1]([C:3]1[CH:40]=[CH:39][C:6]([CH2:7][N:8]2[CH2:21][C@H:22]3[N:23]([CH2:24][CH2:25][CH2:26]3)[C:27]3[N:28]=[C:29]([S:41][CH3:42])[N:30]=[CH:31][C:32]=3[C:33]2=[O:35])=[CH:5][CH:4]=1)#[N:2]

Participants

Conditions

Temperature: 75 °C

Procedure

Ethyl (S)-4-(2-{[(4-cyanobenzyl)(2-nitrobenzenesulfonyl)amino]methyl}pyrrolidin-1-yl)-2-methylthiopyrimidine-5-carboxylate (1.85 g, 3.10 mmol) obtained in Step 1 was dissolved in DMF/ethanol=1/1 (20 mL), and the mixture was stirred at 75° C. for 1.5 hours after adding mercaptoacetic acid (0.647 mL, 9.30 mmol) and DBU (2.78 mL, 18.6 mmol). The reaction mixture was diluted with ethyl acetate, and washed with an aqueous sodium bicarbonate solution and saturated brine. The organic layer was then dried over anhydrous magnesium sulfate. The residue obtained upon concentration was purified by silica gel column chromatography to give (S)-5-(4-cyanobenzyl)-9-methylthio-1,2,3,3a,4,5-hexahydro-5,8,10,10b-tetraazabenzo[e]azulen-6-one (1.12 g, quantitative).

Workup

washwashed with an aqueous sodium bicarbonate solution and saturated brine
dry with materialThe organic layer was then dried over anhydrous magnesium sulfate
customThe residue obtained upon concentration
customwas purified by silica gel column chromatography

Sources & evidence

ORD record: ord-bf3296c0f1c64ac3b040e9668abd38d2
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07998954B2

Reaction notes

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