Acetic Acid → HCID 16728075, compound

HRID 897376Notes

Reaction equation

HRID 897376 reaction equation
CC1C=CC(S([O:11][C:12]2[C:13]([C:30]([NH:32][CH2:33][C:34]3[CH:39]=[CH:38][C:37]([F:40])=[CH:36][C:35]=3[S:41]([N:44]([CH3:46])[CH3:45])(=[O:43])=[O:42])=[O:31])=[N:14][C:15]([N:22]3[CH2:27][CH2:26][CH2:25][CH2:24][S:23]3(=[O:29])=[O:28])=[C:16]3[C:21]=2[N:20]=[CH:19][CH:18]=[CH:17]3)(=O)=O)=CC=1.C[O-].[Na+].C(O)(=O)C.C(O)C>CN(C=O)C.CO>[CH3:45][N:44]([CH3:46])[S:41]([C:35]1[CH:36]=[C:37]([F:40])[CH:38]=[CH:39][C:34]=1[CH2:33][NH:32][C:30]([C:13]1[C:12]([OH:11])=[C:21]2[C:16]([CH:17]=[CH:18][CH:19]=[N:20]2)=[C:15]([N:22]2[CH2:27][CH2:26][CH2:25][CH2:24][S:23]2(=[O:29])=[O:28])[N:14]=1)=[O:31])(=[O:43])=[O:42]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 702EthanolHCID 10942334Sodium MethoxideHCID 86587470HCID 86587470, compound

Product 1

HCID 16728075HCID 16728075, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

Dissolved 7-[({2-[(dimethylamino)sulfonyl]-4-fluorobenzyl}amino)carbonyl]-5-(1,1-dioxido-1,2-thiazinan-2-yl)-1,6-naphthyridin-8-yl 4-methylbenzenesulfonate (271 mg, 0.39 mmol) in DMF (0.5 mL) and added to a solution of sodium methoxide (53 mg, 0.98 mmol) in methanol (3.0 mL). The reaction was stirred at 50° C. for one hour, cooled, and glacial acetic acid (56 μL, 0.78 mmol) was added. The reaction was stripped down three times from methanol. Ethanol was added while sonicating the flask to crash out the product. Collected the solids by vacuum filtration to afford the desired compound as a yellowish solid.

Workup

  1. temperaturecooled
  2. customwhile sonicating the flask
  3. customCollected the solids
  4. filtrationby vacuum filtration

Sources & evidence

ORD record
ord-c775e95c13f5416d927d95ed167612f1
Source dataset
uspto-grants-2005_07
Patent number
US06921759B2

Reaction notes

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