Lithium hydroxide, monohydrate → HCID 178525548, compound

HRID 1713732Notes

Reaction equation

HRID 1713732 reaction equation
O.[OH-].[Li+].[N:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:11]1[O:15][C:14]([C:16]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([C@H:25]3[CH2:30][CH2:29][C@H:28]([CH2:31][C:32]([O:34]C)=[O:33])[CH2:27][CH2:26]3)=[CH:21][CH:20]=2)=[O:17])=[N:13][N:12]=1>O.C1COCC1>[N:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:11]1[O:15][C:14]([C:16]([NH:18][C:19]2[CH:20]=[CH:21][C:22]([C@H:25]3[CH2:26][CH2:27][C@H:28]([CH2:31][C:32]([OH:34])=[O:33])[CH2:29][CH2:30]3)=[CH:23][CH:24]=2)=[O:17])=[N:13][N:12]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 178500659HCID 178500659, compound

Product 1

HCID 178525548HCID 178525548, compoundYield 39.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

Lithium hydroxide monohydrate (60 mg) in water (2 mL) was added to a stirred suspension of methyl {trans-4-[4-({[5-(pyridin-2-ylamino)-1,3,4-oxadiazol-2-yl]carbonyl}amino)phenyl]cyclohexyl}acetate (Example 105, 309 mg) in THF (7 mL). After 16 hours the solution was heated to 40° C. and stirred for a further 5 hours then allowed to cool to ambient temperature. The THF was removed in vacuo and the residue was acidified with 2M HCl. The precipitate was filtered off, washed with ether, warm DCM and warm ether then dried overnight. The resultant solid was purified by HPLC using a gradient of 5-25% MeCN in water with 1% ammonia as the eluent to give the title compound (119 mg) as a solid; 1H NMR δ 10.80 (1H, bs), 10.91 (1H, s), 8.31 (1H, d), 7.86 (2H, m), 7.69 (2H, d), 7.23 (2H, d), 7.05 (1H, m), 2.45 (1H+DMSO, m), 2.14 (2H, d), 1.82 (5H, m), 1.47 (2H, m), 1.13 (2H, m); MS m/e MH+ 422.

Workup

  1. temperatureto cool to ambient temperature
  2. customThe THF was removed in vacuo
  3. filtrationThe precipitate was filtered off
  4. washwashed with ether
  5. temperaturewarm DCM
  6. temperaturewarm ether
  7. customthen dried overnight
  8. customThe resultant solid was purified by HPLC

Sources & evidence

ORD record
ord-2fc2bb81728346219727ff46eaefe84d
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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