Sodium Hydroxide → HCID 57590768, compound

HRID 1783838Notes

Reaction equation

HRID 1783838 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:9]2[N:10]=[C:11]3[N:15]([C:16]=2[C:17]2[CH:22]=[CH:21][N:20]=[C:19]([NH:23][C@@H:24]4[CH2:29][CH2:28][CH2:27][N:26]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:25]4)[N:18]=2)[CH:14]=[CH:13][S:12]3)[CH:6]=[CH:7][CH:8]=1)#[N:2].[OH-:37].[Na+]>C(O)C>[C:33]([O:32][C:30]([N:26]1[CH2:27][CH2:28][CH2:29][C@@H:24]([NH:23][C:19]2[N:18]=[C:17]([C:16]3[N:15]4[C:11]([S:12][CH:13]=[CH:14]4)=[N:10][C:9]=3[C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([C:1](=[O:37])[NH2:2])[CH:4]=3)[CH:22]=[CH:21][N:20]=2)[CH2:25]1)=[O:31])([CH3:36])([CH3:35])[CH3:34]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57463075HCID 57463075, compound

Product 1

HCID 57590768HCID 57590768, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of tert-butyl (3R)-3-({4-[6-(3-cyanophenyl)imidazo[2,1-b][1,3]thiazol-5-yl]pyrimidin-2-yl}amino)piperidine-1-carboxylate (0.204 g, 0.407 mmol) in ethanol (5 mL) was added 25% aqueous sodium hydroxide (0.072 mL, 0.448 mmol). The mixture was heated at 75° C. for 20 hours. Solvent was removed to dryness. Residue was taken into dichloromethane (20 mL), washed with water (5 mL), dried over sodium sulfate and concentrated. Product was purified by flash chromatography on silica gel eluting with 5% methanol in dichloromethane to afford 0.175 g (83%) of the title compound as an off-white solid. M.p.=161-165° C. 400 MHz 1H NMR (DMSO-d6 at 60° C.) δ: 8.70 (br. s, 1H), 8.14 (s, 1H), 8.10 (d, J=5.6 Hz, 1H), 7.94 (d, J=8.0 Hz, 1H), 7.72 (d, J=7.6 Hz, 1H). 7.54(t, J=7.6 Hz, 1H), 7.44 (d, J=4.4 Hz, 1H), 7.30-7.14 (bs, 2H), 7.15 (d, J=6.8 Hz, 1H), 6.33 (d, J=5.2 Hz, 1H), 3.96 (bs, 1H), 3.81-3.77 (m, 1H), 3.68 (bs, 1H), 2.94-2.90 (m, 2H), 2.00-1.97 (m, 1H), 1.80-1.77 (m, 1H), 1.59-1.53 (m, 1H), 1.46-1.40 (m, 1H), 1.34 (s, 9H); LCMS: 520 [M+H].

Workup

  1. customSolvent was removed to dryness
  2. washwashed with water (5 mL)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customProduct was purified by flash chromatography on silica gel eluting with 5% methanol in dichloromethane

Sources & evidence

ORD record
ord-6a9f8a3a7f83409f943a9a3f4b8447eb
Source dataset
uspto-grants-2009_03
Patent number
US07501430B2

Reaction notes

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