Methyl N-(triethylammoniosulfonyl)carbamate → HCID 71577056, compound

HRID 1630343Notes

Reaction equation

HRID 1630343 reaction equation
[C:1]([NH:4][NH:5][C:6](=[O:29])[C:7]1[CH:12]=[C:11]([Cl:13])[C:10]([NH:14][C:15]2[N:20]=[C:19]([NH:21][CH3:22])[C:18]([C:23]([F:26])([F:25])[F:24])=[CH:17][N:16]=2)=[CH:9][C:8]=1[O:27][CH3:28])(=O)[CH3:2].COC(=NS([N+](CC)(CC)CC)(=O)=O)[O-]>C1COCC1>[Cl:13][C:11]1[CH:12]=[C:7]([C:6]2[O:29][C:1]([CH3:2])=[N:4][N:5]=2)[C:8]([O:27][CH3:28])=[CH:9][C:10]=1[NH:14][C:15]1[N:20]=[C:19]([NH:21][CH3:22])[C:18]([C:23]([F:26])([F:25])[F:24])=[CH:17][N:16]=1

Participants

4

Reactant 2

HCID 2724994Methyl N-(triethylammoniosulfonyl)carbamate2×HCID 86688210Benzoic acid, 5-chloro-2-methoxy-4-[[4-(methylamino)-5-(trifluoromethyl)-2-pyrimidinyl]amino]-, 2-acetylhydrazide

Product 1

HCID 71577056HCID 71577056, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of N′-acetoyl-5-chloro-2-methoxy-4-(4-(methylamino)-5-(trifluoromethyl)pyrimidin-2-ylamino)benzohydrazide (68 mg, 0.16 mmol), and 1-methoxy-N-triethylammoniosulfonyl-methanimidate (Burgess reagent) (75 mg, 0.32 mmol) in THF (4 mL) was irradiated in the microwave at 150° C. for 30 min. An additional portion of Burgess reagent (75 mg, 0.32 mmol) was added and the reaction was irradiated a further 30 min at 150° C. in the microwave. The reaction mixture was concentrated and the crude residue purified via silica gel column chromatography (0-100% ethyl acetate/isohexane) to afford a residue that was triturated with diethyl ether/methanol yielding N2-(2-chloro-5-methoxy-4-(5-methyl-1,3,4-oxadiazol-2-yl)phenyl)-N4-methyl-5-(trifluoromethyl)pyrimidine-2,4-diamine as a white solid (28 mg, 43%). HPLC (15 cm_Formic_Ascentis_HPLC_CH3CN): at 9.15 min. LCMS (10 cm_ESCI_Formic_MeCN): [MH+]=415 at 4.00 min. 1H NMR (400 MHz, CDCl): δ 8.62 (s, 1H); 8.25 (s, 1H); 7.95 (s, 1H); 7.80 (s, 1H); 5.34 (s, 1H); 4.01 (s, 3H); 3.15 (d, J=4.7, 3H); 2.61 (s, 3H).

Workup

  1. customwas irradiated in the microwave at 150° C. for 30 min
  2. customthe reaction was irradiated a further 30 min at 150° C. in the microwave
  3. concentrationThe reaction mixture was concentrated
  4. customthe crude residue purified via silica gel column chromatography (0-100% ethyl acetate/isohexane)
  5. customto afford a residue that
  6. customwas triturated with diethyl ether/methanol

Sources & evidence

ORD record
ord-c178ae8081a14fd79efbc23bac313aba
Source dataset
uspto-grants-2014_07
Patent number
US08791130B2

Reaction notes

Loading…