Dichloromethane → 1-[(2,2-Difluorocyclopropyl)methyl]-5-(1,2,3,3a,4,6a-hexahydrocyclo-penta-[c]pyrrol-5-yl)-3-methyl-1,3-dihydro[1,2,5]thiadiazolo[3,4-b]pyridine 2,2-dioxide

HRID 629894Notes

Reaction equation

HRID 629894 reaction equation
[F:1][C:2]1([F:33])[CH2:4][CH:3]1[CH2:5][N:6]1[C:14]2[C:9](=[N:10][C:11]([C:15]3[CH2:16][CH:17]4[CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][CH:18]4[CH:29]=3)=[CH:12][CH:13]=2)[N:8]([CH3:30])[S:7]1(=[O:32])=[O:31].C(Cl)Cl.C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>C(OCC)(=O)C>[F:33][C:2]1([F:1])[CH2:4][CH:3]1[CH2:5][N:6]1[C:14]2[C:9](=[N:10][C:11]([C:15]3[CH2:16][CH:17]4[CH2:21][NH:20][CH2:19][CH:18]4[CH:29]=3)=[CH:12][CH:13]=2)[N:8]([CH3:30])[S:7]1(=[O:32])=[O:31]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 71140780HCID 71140780, compound

Product 1

HCID 711367261-[(2,2-Difluorocyclopropyl)methyl]-5-(1,2,3,3a,4,6a-hexahydrocyclo-penta-[c]pyrrol-5-yl)-3-methyl-1,3-dihydro[1,2,5]thiadiazolo[3,4-b]pyridine 2,2-dioxide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl 5-{1-[(2,2-difluorocyclopropyl)methyl]-3-methyl-2,2-dioxido-1,3-dihydro[1,2,5]thiadiazolo[3,4-b]pyridin-5-yl}-3,3a,4,6a-tetrahydrocyclopenta[c]-pyrrole-2(1H)-carboxylate (24-1, 1.7 g, 3.4 mmol) was added to a mixture of DCM (28 mL) and TFA (7 mL) and stirred for 60 min. Following this duration, the contents were cautiously added to a mixture of saturated NaHCO3 (50 mL) and ethyl acetate (50 mL). The layers were separated and the aqueous layer was back-extracted with ethyl acetate (2×30 mL). The combined organics were dried over Na2SO4, filtered and concentrated in vacuo to give an orange semi-solid. The material was carried forward without further purification.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was back-extracted with ethyl acetate (2×30 mL)
  3. dry with materialThe combined organics were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give an orange semi-solid
  7. customThe material was carried forward without further purification

Sources & evidence

ORD record
ord-164836ac48c14a92aa834de512dcf4a1
Source dataset
uspto-grants-2016_04
Patent number
US09315518B2

Reaction notes

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