2-tert-Butyl-1,1,3,3-tetramethylguanidine → HCID 72194696, compound

HRID 594169Notes

Reaction equation

HRID 594169 reaction equation
[CH3:1][CH:2]([CH3:15])[CH2:3][NH:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([C:11]([F:14])([F:13])[F:12])[N:6]=1.[CH3:16][C:17]1[C:21]([CH2:22][O:23][C:24]2[CH:29]=[CH:28][C:27]([S:30](Cl)(=[O:32])=[O:31])=[CH:26][CH:25]=2)=[C:20]([CH3:34])[O:19][N:18]=1.C(N=C(N(C)C)N(C)C)(C)(C)C>N1C=CC=CC=1>[CH3:16][C:17]1[C:21]([CH2:22][O:23][C:24]2[CH:25]=[CH:26][C:27]([S:30]([N:4]([CH2:3][CH:2]([CH3:15])[CH3:1])[C:5]3[CH:10]=[CH:9][N:8]=[C:7]([C:11]([F:12])([F:14])[F:13])[N:6]=3)(=[O:32])=[O:31])=[CH:28][CH:29]=2)=[C:20]([CH3:34])[O:19][N:18]=1

Participants

5

Reactant 3

HCID 35715812-tert-Butyl-1,1,3,3-tetramethylguanidineHCID 164907024-((3,5-Dimethylisoxazol-4-yl)methoxy)benzene-1-sulfonyl chlorideHCID 89876049HCID 89876049, compound

Product 1

HCID 72194696HCID 72194696, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of N-(2-methylpropyl)-2-(trifluoromethyl)-4-pyrimidinamine (100 mg, 0.456 mmol) and 4-{[(3,5-dimethyl-4-isoxazolyl)methyl]oxy}benzenesulfonyl chloride (151 mg, 0.502 mmol) in pyridine (1 mL) was added 2-(tert-butyl)-1,1,3,3-tetramethylguanidine (0.092 mL, 0.456 mmol). The reaction vessel was sealed and heated by microwaves to 100° C. for 30 minutes. The solvent was evaporated in vacuo to give the crude product, which was purified by solid phase extraction (SPE) using an aminopropyl (NH2) cartridge then a sulphonic acid (SCX) cartridge (both eluted with methanol). The appropriate fractions were combined and dried under a stream of nitrogen to give the crude product which was further purified by mass directed autoprep (formic acid modifier) to give the title product, 19.8 mg. LCMS (2 min, formic) Rt 1.32 min, m/z (ES+) 485 (M+H).

Workup

  1. customThe reaction vessel was sealed
  2. customThe solvent was evaporated in vacuo
  3. customto give the crude product, which
  4. customwas purified by solid phase extraction (SPE)
  5. washa sulphonic acid (SCX) cartridge (both eluted with methanol)
  6. customdried under a stream of nitrogen
  7. customto give the crude product which
  8. customwas further purified by mass

Sources & evidence

ORD record
ord-ca8285e440b049e0b804d18670c43b55
Source dataset
uspto-grants-2016_01
Patent number
US09242972B2

Reaction notes

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