Methyl N-(triethylammoniosulfonyl)carbamate → HCID 86615703, compound

HRID 2110732Notes

Reaction equation

HRID 2110732 reaction equation
[C:1]([NH:4][NH:5][C:6](=[O:25])[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][NH:15][C:16]2[CH:21]=[C:20]([Cl:22])[N:19]=[C:18]([O:23][CH3:24])[N:17]=2)=[CH:9][CH:8]=1)(=O)[CH3:2].CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC>C1COCC1>[Cl:22][C:20]1[N:19]=[C:18]([O:23][CH3:24])[N:17]=[C:16]([NH:15][CH2:14][CH2:13][C:10]2[CH:9]=[CH:8][C:7]([C:6]3[O:25][C:1]([CH3:2])=[N:4][N:5]=3)=[CH:12][CH:11]=2)[CH:21]=1

Participants

4

Reactant 2

HCID 2724994Methyl N-(triethylammoniosulfonyl)carbamateHCID 86615702HCID 86615702, compound

Product 1

HCID 86615703HCID 86615703, compoundYield 84.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-[2-(6-chloro-2-methoxy-pyrimidin-4-ylamino)-ethyl]-benzoic acid N′-acetyl-hydrazide (0.2 g, 0.55 mmol), and Burgess reagent (0.39 g, 1.65 mmol) in THF (6 mL) is placed in a microwave reactor. After 5 min at 130° C., the mixture is concentrated in a rotavap, and subjected to a chromatography eluting with 10% MeOH in CH2Cl2 to afford (6-chloro-2-methoxy-pyrimidin-4-yl)-{2-[4-(5-methyl-[1,3,4]oxadiazol-2-yl)-phenyl]-ethyl}-amine (160 mg). LCMS: RT=2.29 minutes; MS: 346 (M+H).

Workup

  1. customis placed in a microwave reactor
  2. concentrationthe mixture is concentrated in a rotavap
  3. washeluting with 10% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-8f6325e6eb434d57aa7e4a61047a4bde
Source dataset
uspto-grants-2009_04
Patent number
US07517889B2

Reaction notes

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