2-tert-Butyl-1,1,3,3-tetramethylguanidine → HCID 86731580, compound

HRID 1746399Notes

Reaction equation

HRID 1746399 reaction equation
Cl.[CH:2]1([CH2:5][C:6]2[CH:11]=[C:10]([CH3:12])[C:9]([NH2:13])=[C:8]([CH3:14])[CH:7]=2)[CH2:4][CH2:3]1.[CH3:15][C:16]1[C:20]([CH2:21][O:22][C:23]2[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:24]=2)=[C:19]([CH3:33])[O:18][N:17]=1.C(N=C(N(C)C)N(C)C)(C)(C)C>N1C=CC=CC=1.CO>[CH:2]1([CH2:5][C:6]2[CH:7]=[C:8]([CH3:14])[C:9]([NH:13][S:29]([C:26]3[CH:25]=[CH:24][C:23]([O:22][CH2:21][C:20]4[C:16]([CH3:15])=[N:17][O:18][C:19]=4[CH3:33])=[CH:28][CH:27]=3)(=[O:30])=[O:31])=[C:10]([CH3:12])[CH:11]=2)[CH2:3][CH2:4]1

Participants

6

Reactant 3

HCID 35715812-tert-Butyl-1,1,3,3-tetramethylguanidineHCID 164907024-((3,5-Dimethylisoxazol-4-yl)methoxy)benzene-1-sulfonyl chlorideHCID 68671668HCID 68671668, compound

Product 1

HCID 86731580HCID 86731580, compoundYield 3.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 1049PyridineSolvent

Procedure

To a solution of [4-(cyclopropylmethyl)-2,6-dimethylphenyl]amine hydrochloride (100 mg, 0.472 mmol) and 4-{[(3,5-dimethyl-4-isoxazolyl)methyl]oxy}benzenesulfonyl chloride (157 mg, 0.520 mmol) in Pyridine (1 mL) was added neat Barton's base (2-(tert-butyl)-1,1,3,3-tetramethylguanidine) (0.095 mL, 0.472 mmol). The reaction vessel was sealed and heated in Emrys Optimiser using initial high absorbance to 100° C. for 30 min. After cooling the reaction was analysed and product presence confirmed. The solvent was evaporated in vacuo using the Vaportec V10 to give the crude product. The sample was loaded in methanol and purified by SPE on aminopropyl (NH2) 5 g using methanol. The appropriate fractions were concentrated and the crude material further purified by SPE on sulfonic acid (SCX) 2 g using methanol. The appropriate fractions were combined and dried under a stream of nitrogen in the Radleys blowdown apparatus to give the crude product. The samples were dissolved in 1:1 MeOH:DMSO 1 mL and purified by mass directed autoPrep on Sunfire C18 column using Acetonitrile Water with a Formic acid modifier. The solvent was dried under a stream of nitrogen in the Radleys blowdown apparatus to give the required products (7.4 mg, 0.017 mmol, 3.56% yield)

Workup

  1. customThe reaction vessel was sealed
  2. temperatureheated in Emrys Optimiser
  3. customto 100° C.
  4. customfor 30 min
  5. temperatureAfter cooling the reaction
  6. customThe solvent was evaporated in vacuo
  7. customto give the crude product
  8. custompurified by SPE on aminopropyl (NH2) 5 g
  9. concentrationThe appropriate fractions were concentrated
  10. customthe crude material further purified by SPE on sulfonic acid (SCX) 2 g
  11. customdried under a stream of nitrogen in the Radleys blowdown apparatus
  12. customto give the crude product
  13. customDMSO 1 mL and purified by mass
  14. customThe solvent was dried under a stream of nitrogen in the Radleys blowdown apparatus

Sources & evidence

ORD record
ord-429127b5234a4e889386ebbe36bfa683
Source dataset
uspto-grants-2015_10
Patent number
US09150508B2

Reaction notes

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