Hydrochloric Acid → 2-(4-(2-(1-(Tert-butoxycarbonyl)piperidin-4-yl)thieno[3,2-b]pyridin-7-yloxy)-3-fluorophenylamino)nicotinic acid

HRID 1676411Notes

Reaction equation

HRID 1676411 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[S:22][C:21]3[C:16](=[N:17][CH:18]=[CH:19][C:20]=3[O:23][C:24]3[CH:29]=[CH:28][C:27]([NH:30][C:31]4[N:41]=[CH:40][CH:39]=[CH:38][C:32]=4[C:33]([O:35]CC)=[O:34])=[CH:26][C:25]=3[F:42])[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].Cl>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[S:22][C:21]3[C:16](=[N:17][CH:18]=[CH:19][C:20]=3[O:23][C:24]3[CH:29]=[CH:28][C:27]([NH:30][C:31]4[N:41]=[CH:40][CH:39]=[CH:38][C:32]=4[C:33]([OH:35])=[O:34])=[CH:26][C:25]=3[F:42])[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67345485Ethyl 2-(4-(2-(1-(tert-butoxycarbonyl)piperidin-4-yl)thieno[3,2-b]pyridin-7-yloxy)-3-fluorophenylamino)nicotinate

Product 1

HCID 673485102-(4-(2-(1-(Tert-butoxycarbonyl)piperidin-4-yl)thieno[3,2-b]pyridin-7-yloxy)-3-fluorophenylamino)nicotinic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A round-bottomed flask was charged with ethyl 2-(4-(2-(1-(tert-butoxycarbonyl)piperidin-4-yl)thieno[3,2-b]pyridin-7-yloxy)-3-fluorophenylamino)nicotinate (0.100 g, 0.169 mmol) and THF (1 mL). NaOH (3.0 mL, 1N) was added and the mixture stirred for 1 hour. The mixture was then acidified to pH 6 with HCl aq. (1N) and extracted with EtOAc. The organics were dried (MgSO4), filtered and concentrated to get product as a yellow solid. LRMS (esi+) 565 m/z (M+1) detected.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organics were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto get product as a yellow solid

Sources & evidence

ORD record
ord-316f2e0fbc2f4b8faafa63954fc5c86f
Source dataset
uspto-grants-2011_08
Patent number
US08003662B2

Reaction notes

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