Sodium hydride → HCID 59681824, compound

HRID 1394217Notes

Reaction equation

HRID 1394217 reaction equation
C(OC(=O)[NH:7][C:8]1[C:12]([C:13]2[N:14]([CH2:38][CH3:39])[C:15]3[C:20]([S:21]([N:24]4[CH2:28][CH2:27][C@H:26]([NH:29]C(OC(C)(C)C)=O)[CH2:25]4)(=[O:23])=[O:22])=[CH:19][N:18]=[CH:17][C:16]=3[N:37]=2)=[N:11][O:10][N:9]=1)(C)(C)C.C(OC(=O)NC1C(C2N(CC)C3C(Br)=CN=CC=3N=2)=NON=1)(C)(C)C.[H-].[Na+].C([Li])CCC>O1CCCC1.N1C=CC=CC=1>[NH2:29][C@H:26]1[CH2:27][CH2:28][N:24]([S:21]([C:20]2[C:15]3[N:14]([CH2:38][CH3:39])[C:13]([C:12]4[C:8]([NH2:7])=[N:9][O:10][N:11]=4)=[N:37][C:16]=3[CH:17]=[N:18][CH:19]=2)(=[O:22])=[O:23])[CH2:25]1

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 596817711,1-Dimethylethyl N-[4-(7-bromo-1-ethyl-1H-imidazo[4,5-c]pyridin-2-yl)-1,2,5-oxadiazol-3-yl]carbamateHCID 69158926HCID 69158926, compoundHCID 178418339Butyllithium

Product 1

HCID 59681824HCID 59681824, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

{4-[7-((S)-3-tert-Butoxycarbonylamino-pyrrolidine-1-sulfonyl)-1-ethyl-1H-imidazo[4,5-c]pyridin-2-yl]-furazan-3-yl)-carbamic acid tert-butyl ester A solution of the product from Example 279 (0.150 g, 0.367 mmol) in tetrahydrofuran (2 ml) at ambient temperature was treated with NaH (60%) under Argon. After 10 minutes, the mixture was cooled to −78° C., and was treated with n-butyllithium. After 10 minutes, the mixture was treated with a SO2 solution (2 mL), formed from bubbling SO2 gas into THF (2 mL). After 10 minutes of stirring, the mixture was treated with SO2Cl2, and was allowed to warm to ambient temperature. The reaction mixture was then concentrtated, in-vacuo, to dryness. The solid was dissolved in dichloromethane (2.5 mL) and pyridine (2.5 mL) under Argon, and was treated with the amine (0.085 g, 0.46 mmol), and was stirred at ambient temperature overnight. The completed reaction was concentrated down to afford the title compound; MS (ES+) m/e 580 [M+H]+. Step 2. 4-[7-((S)-3-Amino-pyrrolidine-1-sulfonyl)-1-ethyl-1H-imidazo[4,5-c]pyridin-2-yl]-furazan-3-ylamine

Workup

  1. waitAfter 10 minutes
  2. customformed
  3. customfrom bubbling SO2 gas into THF (2 mL)
  4. additionthe mixture was treated with SO2Cl2
  5. temperatureto warm to ambient temperature
  6. dissolutionThe solid was dissolved in dichloromethane (2.5 mL)
  7. stirringwas stirred at ambient temperature overnight
  8. customThe completed reaction
  9. concentrationwas concentrated down

Sources & evidence

ORD record
ord-938e1cfff74c445ba0437c9b9c156694
Source dataset
uspto-grants-2008_03
Patent number
US07348339B2

Reaction notes

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