Sodium Sulfate → HCID 44195007, compound

HRID 1878604Notes

Reaction equation

HRID 1878604 reaction equation
C[O:2][C:3](=O)[CH2:4][NH:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]2[CH:14]=[N:15][CH:16]=[C:17]([C:19]3[CH:24]=[C:23]([C:25]4[CH:30]=[CH:29][CH:28]=[C:27]([CH3:31])[N:26]=4)[N:22]=[C:21]4[NH:32][CH:33]=[CH:34][C:20]=34)[CH:18]=2)[CH:8]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[O-]S([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[CH3:31][C:27]1[N:26]=[C:25]([C:23]2[N:22]=[C:21]3[NH:32][CH:33]=[CH:34][C:20]3=[C:19]([C:17]3[CH:18]=[C:13]([C:9]4[CH:8]=[C:7]([CH:12]=[CH:11][CH:10]=4)[CH2:6][NH:5][CH2:4][CH2:3][OH:2])[CH:14]=[N:15][CH:16]=3)[CH:24]=2)[CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 68932169HCID 68932169, compound

Product 1

HCID 44195007HCID 44195007, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (3-{5-[6-(6-methyl-pyridin-2-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-pyridin-3-yl}-benzylamino)-acetic acid methyl ester (Example 131) (1 eq, 0.216 mmol, 100 mg) in THF (2.5 ml) at 0° C. is added LAH (1M in THF, 0.8 eq, 0.173 mmol, 0.173 ml). The resulting suspension is allowed to warm to r.t. and then stirred for 1 h at this temperature. After cooling to 0° C. sat. aqueous Na2SO4 solution is added, and the mixture is stirred for additional 30 min. The suspension is filtered and concentrated under reduced pressure. Addition of 4 M aqueous NaOH solution is followed by extraction with EtOAc. The organic layer is dried with MgSO4, filtered, and concentrated under reduced pressure. The crude product is recrystallized using EtOAc/MeCN to give the title compound; [M+H]+=436; 1H-NMR (400 MHz, CD3OD): δ 8.98 (d, 1H), 8.90 (d, 1H), 8.50 (t, 1H), 8.26 (s, 1H), 8.20 (d, 1H), 7.80-7.76 (m, 2H), 7.68 (d, 1H), 7.56 (d, 1H), 7.50 (t, 1H), 7.43 (d, 1H), 7.25 (d, 1H), 6.70 (d, 1H), 3.89 (s, 2H), 3.69 (t, 2H), 2.77 (t, 2H), 2.62 (s, 3H).

Workup

  1. additionis added
  2. stirringthe mixture is stirred for additional 30 min
  3. filtrationThe suspension is filtered
  4. concentrationconcentrated under reduced pressure
  5. additionAddition of 4 M aqueous NaOH solution
  6. extractionis followed by extraction with EtOAc
  7. dry with materialThe organic layer is dried with MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe crude product is recrystallized

Sources & evidence

ORD record
ord-796045d986804f8c934f9abcc267b63a
Source dataset
uspto-grants-2012_11
Patent number
US08314112B2

Reaction notes

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