Hydrochloric Acid → HCID 178464667, compound

HRID 1396070Notes

Reaction equation

HRID 1396070 reaction equation
Cl.[CH2:2]([NH:4][C:5]([N:7]1[CH2:11][C:10]([CH3:13])([CH3:12])[CH:9]=[N:8]1)=[NH:6])[CH3:3].CCN(P1(N(C)CCCN1C)=NC(C)(C)C)CC.[Br:32][C:33]1[CH:34]=[C:35]([S:46](Cl)(=[O:48])=[O:47])[CH:36]=[CH:37][C:38]=1[NH:39][C:40](=[O:45])[C:41]([F:44])([F:43])[F:42].Cl>C1COCC1>[Br:32][C:33]1[CH:34]=[C:35]([S:46](=[O:48])(=[O:47])[N:6]=[C:5]([N:7]2[CH2:11][C:10]([CH3:12])([CH3:13])[CH:9]=[N:8]2)[NH:4][CH2:2][CH3:3])[CH:36]=[CH:37][C:38]=1[NH:39][C:40](=[O:45])[C:41]([F:43])([F:44])[F:42]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 35138512-((1,1-Dimethylethyl)imino)-N,N-diethylhexahydro-1,3-dimethyl-2lambda5-1,3,2-diazaphosphorin-2-amineHCID 581587063-Bromo-4-(2,2,2-trifluoroacetamido)benzene-1-sulfonyl chlorideHCID 178464603HCID 178464603, compound

Product 1

HCID 178464667HCID 178464667, compoundYield 78.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1.20 g N-ethyl-4,4-dimethyl-4,5-dihydro-pyrazole-1-carboxamidine hydrochloride in 35 mL dry THF was added 5.1 mL (3.0 equiv.) BEMP and the reaction mixture was stirred for 10 minutes at room temperature. 2.15 g (1.0 equiv.) 3-Bromo-4-(2,2,2-trifluoro-acetylamino)-benzenesulfonyl chloride was added in one portion and the resulting bright yellow solution was stirred overnight at room temperature. The reaction mixture was acidified with 1N HCl and extracted twice with EA. The combined organic layers were dried over Na2SO4, filtered and evaporated under reduced pressure. Purification by flash chromatography (Et2O/PA 1:1→Et2O) afforded 2.29 g (78%) of product. 1H NMR (400 MHz, CDCl3) δ 1.18 (t, J=7.3 Hz, 3H), 1.24 (s, 6H), 3.43-3.51 (m, 2H), 3.79 (br.s, 2H), 6.78 (s, 1H), 7.93 (dd, J=8.6, 2.0 Hz, 1H), 8.19 (d, J=2.0 Hz, 1H), 8.39 (d, J=8.6 Hz, 1H), 8.61 (br.s., 1H).

Workup

  1. stirringthe resulting bright yellow solution was stirred overnight at room temperature
  2. extractionextracted twice with EA
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customPurification by flash chromatography (Et2O/PA 1:1→Et2O)

Sources & evidence

ORD record
ord-9e5d5c4c99ff4c4d82e01c57013b1f52
Source dataset
uspto-grants-2014_12
Patent number
US08901108B2

Reaction notes

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