Sodium Hydroxide → 5-(1-(7-(3,4-Dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)piperidine-3-carboxamido)picolinic acid

HRID 1410079Notes

Reaction equation

HRID 1410079 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][C:12]2[C:13]3[N:39]=[CH:38][S:37][C:14]=3[N:15]=[C:16]([N:18]3[CH2:23][CH2:22][CH2:21][CH:20]([C:24]([NH:26][C:27]4[CH:28]=[CH:29][C:30]([C:33]([O:35]C)=[O:34])=[N:31][CH:32]=4)=[O:25])[CH2:19]3)[N:17]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[OH-].[Na+]>O1CCOCC1.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][C:12]2[C:13]3[N:39]=[CH:38][S:37][C:14]=3[N:15]=[C:16]([N:18]3[CH2:23][CH2:22][CH2:21][CH:20]([C:24]([NH:26][C:27]4[CH:28]=[CH:29][C:30]([C:33]([OH:35])=[O:34])=[N:31][CH:32]=4)=[O:25])[CH2:19]3)[N:17]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66549701Methyl 5-(1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)piperidine-3-carboxamido)picolinate

Product 1

HCID 683793295-(1-(7-(3,4-Dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)piperidine-3-carboxamido)picolinic acidYield 76.2%

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
35 °C

Procedure

To a solution of methyl 5-(1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)piperidine-3-carboxamido)picolinate (130 mg, 0.24 mmol) in dioxane/H2O (8 mL/8 mL) was added NaOH (70 mg, 1.75 mmol), the reaction mixture was heated to 35° C. with stirring for 30 minutes, the dioxane was removed in vacuo, and the aqueous layer was adjusted to pH=4-5 with conc. HCl, the precipitate was collected by filtration and washed with methanol (5 mL) to afford 5-(1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)piperidine-3-carboxamido)picolinic acid (98 mg, 76.2%) as an orange solid. 1H NMR (300 MHz, DMSO): δ 10.58 (s, 1H), 9.68 (s, 1H), 8.87 (s, 2H), 8.24 (dd, 1H, J1=8.7 Hz, J2=2.4 Hz), 8.03 (d, 1H, J=8.7 Hz), 7.67 (d, 1H, J=2.1 Hz), 7.35 (dd, 1H, J1=8.7 Hz, J2=2.1 Hz), 6.82 (brs, 1H), 4.84-4.65 (m, 2H), 3.77-3.65 (m, 6H), 3.18-3.00 (m, 2H), 2.67-2.64 (m, 1H), 2.05-1.75 (m, 4H). LC-MS: 536 [M+H]+, tR=1.50 min. HPLC: 97.47% at 214 nm, 97.48% at 254 nm, tR=4.096 min.

Workup

  1. customthe dioxane was removed in vacuo
  2. filtrationthe precipitate was collected by filtration
  3. washwashed with methanol (5 mL)

Sources & evidence

ORD record
ord-6f6d096827c54b9f9b81c0c31384ee1f
Source dataset
uspto-grants-2014_12
Patent number
US08921383B2

Reaction notes

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