Sodium Hydroxide → (6-{[4-(Pyrazol-1-yl)benzyl](pyridin-2-ylsulfonyl)aminomethyl}pyridin-2-ylamino)acetic acid

HRID 241263Notes

Reaction equation

HRID 241263 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]([CH2:26][C:27]2[CH:32]=[CH:31][C:30]([N:33]3[CH:37]=[CH:36][CH:35]=[N:34]3)=[CH:29][CH:28]=2)[NH:16][S:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=2)(=[O:19])=[O:18])[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.[OH-].[Na+]>>[N:33]1([C:30]2[CH:29]=[CH:28][C:27]([CH2:26][CH:15]([NH:16][S:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=3)(=[O:18])=[O:19])[C:11]3[N:10]=[C:9]([NH:8][CH2:7][C:6]([OH:45])=[O:5])[CH:14]=[CH:13][CH:12]=3)=[CH:32][CH:31]=2)[CH:37]=[CH:36][CH:35]=[N:34]1

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 86651780Tert-butyl[tert-butoxycarbonyl(6-{[4-(pyridin-2-yl)benzyl]-(pyridin-3-ylsulfonyl)aminomethyl}pyridin-2-yl)amino]acetateHCID 86651782Tert-butyl [tert-butoxycarbonyl(6-{[4-(pyrazol-1-yl)benzyl](pyridin-2-ylsulfonyl)aminomethyl]pyridin-2-yl)amino}acetate

Product 1

HCID 66717259(6-{[4-(Pyrazol-1-yl)benzyl](pyridin-2-ylsulfonyl)aminomethyl}pyridin-2-ylamino)acetic acidYield 185.4%

Procedure

Reaction was carried out in the same manner as in Example 19-(b) except for using tert-butyl[tert-butoxycarbonyl(6-{[4-(pyrazol-1-yl)benzyl](pyridin-2-ylsulfonyl)aminomethyl}pyridin-2-yl)amino]acetate (440 mg, 0.611 mmol) obtained in Example 21-(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 adjusted to pH 4.5 with a 2N aqueous sodium hydroxide solution, followed by extraction with ethyl acetate. The separated organic layer was dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. To the resulting residue were added ethyl acetate (4 ml) and diisopropyl ether (16 ml), followed by sonication at 40° C. for 15 minutes. The solvent was distilled off under reduced pressure, and then dried under reduced pressure to afford the title compound (542 mg) as a white foam. (Yield: 97%)

Workup

  1. customReaction
  2. customAfter completion of the reaction
  3. extractionfollowed by extraction with ethyl acetate
  4. dry with materialThe separated organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. additionTo the resulting residue were added ethyl acetate (4 ml) and diisopropyl ether (16 ml)
  7. customfollowed by sonication at 40° C. for 15 minutes
  8. distillationThe solvent was distilled off under reduced pressure
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-65b41a9fd87f4d83966d0ee8691f51aa
Source dataset
uspto-grants-2014_02
Patent number
US08648097B2

Reaction notes

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