Water → HCID 57396172, compound

HRID 1177658Notes

Reaction equation

HRID 1177658 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][C:15]=1[C:16]1[S:17][C:18]2[C:23]([N:24]=1)=[CH:22][CH:21]=[C:20]([C:25]1([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH2:27][CH2:26]1)[N:19]=2)[CH2:5][NH:6][CH2:7][C:8]([O:10]CC)=[O:9].O.O.[OH-].[Li+]>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][C:15]=1[C:16]1[S:17][C:18]2[C:23]([N:24]=1)=[CH:22][CH:21]=[C:20]([C:25]1([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[CH2:26][CH2:27]1)[N:19]=2)[CH2:5][NH:6][CH2:7][C:8]([OH:10])=[O:9]

Participants

5

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 67111735HCID 67111735, compound

Product 1

HCID 57396172HCID 57396172, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 2-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)-benzylamino)acetate (80 mg, 0.173 mmol) was dissolved in THF (1.4 mL) and water (347 μL) before lithium hydroxide monohydrate (21.82 mg, 0.520 mmol) was added and stirred at ambient temperature for 16 h. The reaction mixture was concentrated, acidified to pH 7 with 1 N HCl, filtered, and washed with water, DMSO, then water, and dried in a vacuum oven to give the title compound. MS (ESI) m/z: Calculated: 433.1; Observed: 433.8 (M++H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. filtrationfiltered
  3. washwashed with water, DMSO
  4. dry with materialwater, and dried in a vacuum oven

Sources & evidence

ORD record
ord-ebd7a30648a2469fa58137f0ee904bea
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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