HCID 18771682, compound → HCID 18771992, compound

HRID 479691Notes

Reaction equation

HRID 479691 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[N:7]1[CH:12]=[CH:11][C:10]([C:13]2[S:14][CH:15]=[C:16]([NH:18][C:19](=[O:37])[NH:20][C:21]3[N:26]=[C:25]([CH2:27][N:28]4[CH2:32][CH2:31][CH2:30][CH:29]4[C:33](OC)=[O:34])[CH:24]=[CH:23][CH:22]=3)[N:17]=2)=[CH:9][CH:8]=1>C1COCC1>[OH:34][CH2:33][CH:29]1[CH2:30][CH2:31][CH2:32][N:28]1[CH2:27][C:25]1[N:26]=[C:21]([NH:20][C:19]([NH:18][C:16]2[N:17]=[C:13]([C:10]3[CH:9]=[CH:8][N:7]=[CH:12][CH:11]=3)[S:14][CH:15]=2)=[O:37])[CH:22]=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 18771682HCID 18771682, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 18771992HCID 18771992, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

LiAlH4 (3 mg, 0.079 mmol) was added to a solution of methyl 1-{6-[3-(2-pyridin-4-yl-thiazol-4-yl)ureido]-pyridin-2-ylmethyl}-pyrrolidine-2-carboxylate (15 mg, 0.034 mmol, Example 77) in THF (5 mL) at RT and the resulting mixture was stirred for 8 h. A precipitate formed and was collected. The solid was dissolved in CHCl3 (5 mL) and washed with saturated NaHCO3 solution (5 mL). The aqueous layer was adjusted to pH 7 with 1N HCl and extracted with CHCl3. The organics were combined, dried over MgSO4 and concentrated in vacuo to give a pale yellow solid. MS m/z: 411.1 (M+H). Calc'd for C20H22N6O2S-410.50.

Workup

  1. customA precipitate formed
  2. customwas collected
  3. dissolutionThe solid was dissolved in CHCl3 (5 mL)
  4. washwashed with saturated NaHCO3 solution (5 mL)
  5. extractionextracted with CHCl3
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customto give a pale yellow solid

Sources & evidence

ORD record
ord-76507fa2e9a04cf3b28ad21b2e4878fe
Source dataset
uspto-grants-2003_11
Patent number
US06645990B2

Reaction notes

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