Tert-butyl[tert-butoxycarbonyl(6-{[4-(pyridin-2-yl)benzyl]-(pyridin-3-ylsulfonyl)aminomethyl}pyridin-2-yl)amino]acetate → (6-{(Pyridin-3-ylsulfonyl)[4-(1,2,4-triazol-1-yl)benzyl]aminomethyl}pyridin-2-ylamino)acetic acid

HRID 241262Notes

Reaction equation

HRID 241262 reaction equation
C([O:5][C:6](=[O:45])[CH2:7][N:8](C(OC(C)(C)C)=O)[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH:15]([S:29]([C:32]2[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=2)(=[O:31])=[O:30])[NH:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([N:24]3[CH:28]=[N:27][CH:26]=[N:25]3)=[CH:20][CH:19]=2)[N:10]=1)(C)(C)C.C(OC(=O)CN(C(OC(C)(C)C)=O)C1C=CC=C(C(CC2C=CC(C3C=CC=CN=3)=CC=2)NS(C2C=NC=CC=2)(=O)=O)N=1)(C)(C)C>>[N:34]1[CH:35]=[CH:36][CH:37]=[C:32]([S:29]([CH:15]([NH:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([N:24]3[CH:28]=[N:27][CH:26]=[N:25]3)=[CH:20][CH:19]=2)[C:11]2[N:10]=[C:9]([NH:8][CH2:7][C:6]([OH:45])=[O:5])[CH:14]=[CH:13][CH:12]=2)(=[O:30])=[O:31])[CH:33]=1

Participants

3

Reactant 2

HCID 86651780Tert-butyl[tert-butoxycarbonyl(6-{[4-(pyridin-2-yl)benzyl]-(pyridin-3-ylsulfonyl)aminomethyl}pyridin-2-yl)amino]acetateHCID 86651781Tert-butyl [tert-butoxycarbonyl(6-{(pyridin-3-ylsulfonyl)[4-(1,2,4-triazol-1-yl)benzyl]aminomethyl}pyridin-2-yl)amino]acetate

Product 1

HCID 66717686(6-{(Pyridin-3-ylsulfonyl)[4-(1,2,4-triazol-1-yl)benzyl]aminomethyl}pyridin-2-ylamino)acetic acidYield 88%

Conditions

Temperature
50 °C

Procedure

Reaction was carried out in the same manner as in Example 19-(b) except for using tert-butyl[tert-butoxycarbonyl(6-{(pyridin-3-ylsulfonyl)[4-(1,2,4-triazol-1-yl)benzyl]aminomethyl}pyridin-2-yl)amino]acetate (936 mg, 1.47 mmol) obtained in Example 20-(a) in place of tert-butyl[tert-butoxycarbonyl(6-{[4-(pyridin-2-yl)benzyl]-(pyridin-3-ylsulfonyl)aminomethyl}pyridin-2-yl)amino]acetate. After completion of the reaction, the reaction solution was concentrated under reduced pressure. The concentrate was adjusted to pH 4.5 with a 6N aqueous sodium hydroxide solution, and a precipitated solid was collected by filtration. Acetone (1.3 ml) was added to the crude product, followed by stirring at 50° C. for 1 hour, and then at room temperature for 1 hour. A precipitated solid was collected by filtration, and then dried under reduced pressure to afford the title compound (618 mg) as a white solid. (Yield: 88%)

Workup

  1. customReaction
  2. customAfter completion of the reaction
  3. concentrationthe reaction solution was concentrated under reduced pressure
  4. filtrationa precipitated solid was collected by filtration
  5. additionAcetone (1.3 ml) was added to the crude product
  6. waitat room temperature for 1 hour
  7. filtrationA precipitated solid was collected by filtration
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-2e5d7cd549bd4b1d900851b96ac05360
Source dataset
uspto-grants-2014_02
Patent number
US08648097B2

Reaction notes

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