Potassium Hydroxide → HCID 59539017, compound

HRID 2039781Notes

Reaction equation

HRID 2039781 reaction equation
[OH-].[K+].C([O:5][C:6](=[O:33])[CH2:7][O:8][CH2:9][C:10]1[CH:32]=[C:13]2[C:14]([C:18](=[O:31])[NH:19][CH2:20][C:21]34[CH2:30][CH:25]5[CH2:26][CH:27]([CH2:29][CH:23]([CH2:24]5)[CH2:22]3)[CH2:28]4)=[CH:15][CH:16]=[CH:17][N:12]2[N:11]=1)C>CCO>[C:21]12([CH2:20][NH:19][C:18]([C:14]3[C:13]4[N:12]([N:11]=[C:10]([CH2:9][O:8][CH2:7][C:6]([OH:33])=[O:5])[CH:32]=4)[CH:17]=[CH:16][CH:15]=3)=[O:31])[CH2:30][CH:25]3[CH2:24][CH:23]([CH2:29][CH:27]([CH2:26]3)[CH2:28]1)[CH2:22]2

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 25095104{4-[(Adamantan-1-ylmethyl)carbamoyl]pyrazolo[1,5-a]pyridin-2-ylmethoxy}acetic acid ethyl ester

Product 1

HCID 59539017HCID 59539017, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3 M Aq. KOH (50 μL) is added to a solution of {4-[(adamantan-1-ylmethyl)carbamoyl]-pyrazolo[1,5-a]pyridin-2-ylmethoxy}acetic acid ethyl ester (11 mg, 25 μmol) and EtOH (250 μL). After 18 h, the volatiles are removed under reduced pressure. The residue is diluted with H2O (0.3 mL) and then acidified with 1 M aq. HCl. The title compound is collected by filtration. 1H NMR (400 MHz, ((CD3)2SO) δ: 8.74 (d, 1H), 8.42 (bs, 1H), 7.62 (d, 1H), 6.93 (t, 1H), 6.84 (s, 1H), 4.70 (s, 2H), 4.08 (s, 2H), 2.99 (d, 2H), 1.86-2.00 (m, 3H), 1.48-1.73 (m, 12H). LC-MS m/z (M+H+): 398.3; RT=1.26.

Workup

  1. customthe volatiles are removed under reduced pressure
  2. additionThe residue is diluted with H2O (0.3 mL)
  3. filtrationThe title compound is collected by filtration
  4. customRT=1.26

Sources & evidence

ORD record
ord-dbcef0cbb8984d3d82956851d434eac4
Source dataset
uspto-grants-2013_11
Patent number
US08580812B2

Reaction notes

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