Sodium Carbonate → HCID 86616714, compound

HRID 1783836Notes

Reaction equation

HRID 1783836 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:16][CH2:15][CH2:14][C@@H:13]([NH:17][C:18]3[N:23]=[C:22]([C:24]4[N:31]5[C:27]([S:28][CH:29]=[CH:30]5)=[N:26][C:25]=4[C:32]4[CH:37]=[CH:36][CH:35]=[C:34]([C:38]#[N:39])[CH:33]=4)[CH:21]=[CH:20][N:19]=3)[CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.Cl.[NH2:41][OH:42].C(=O)([O-])[O-].[Na+].[Na+]>C(O)C.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:16][CH2:15][CH2:14][C@@H:13]([NH:17][C:18]3[N:23]=[C:22]([C:24]4[N:31]5[C:27]([S:28][CH:29]=[CH:30]5)=[N:26][C:25]=4[C:32]4[CH:33]=[C:34]([C:38](=[N:41][OH:42])[NH2:39])[CH:35]=[CH:36][CH:37]=4)[CH:21]=[CH:20][N:19]=3)[CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 57463153HCID 57463153, compound

Product 1

HCID 86616714HCID 86616714, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of N-{(3R)-1-[(4-chlorophenyl)sulfonyl]piperidin-3-yl}-4-[6-(3-cyano-phenyl)imidazo[2,1-b][1,3]thiazol-5-yl]pyrimidin-2-amine (0.050 g, 0.086 mmol) in 80% ethanol-water (2.5 mL) was added an aqueous solution (0.50 mL) containing 6.65 mg of hydroxylamine hydrochloride (1.1 equivalents) and 4.61 mg of sodium carbonate (0.5 equivalents). The resulting solution was heated at 80° C. for 20 hours. Solid was collected by filtration and treated with hot (80° C.) 80% ethanol-water (2 mL×5). Solid was collected and dried under vacuum at 45° C. overnight to afford 25 mg (48%) of the title compound as a yellow solid. M.p.=272-273° C. 400 MHz 1H NMR (DMSO-d6 at 60° C.) δ: 9.52 (s, 1H), 8.70 (bs, 1H), 8.11 (d, J=5.2 Hz, 1H), 7.93 (s, 1H), 7.77-7.73 (m, 3H), 7.67-7.66 (m, 2H), 7.59 (d, J=6.8 Hz, 1H), 7.47-7.40 (m, 2H), 7.11 (d, J=7.6 Hz, 1H), 6.38 (d, J=4.4 Hz, 1H), 5.68 (s, 2H), 3.94 (br. s, 1H), 3.73 (d, J=8.4 Hz, 1H), 3.48 (d, J=10.8 Hz, 1H), 2.49-2.48 (m, 1H), 2.35 (t, J=8.8 Hz, 1H), 1.95-1.84 (m, 2H), 1.60-1.5 (m, 1H), 1.46-1.30 (m, 1H). LCMS: 610 [M+H].

Workup

  1. filtrationSolid was collected by filtration
  2. additiontreated with hot (80° C.) 80% ethanol-water (2 mL×5)
  3. customSolid was collected
  4. customdried under vacuum at 45° C. overnight

Sources & evidence

ORD record
ord-565e1347ed214a0ab82f06521329a8dd
Source dataset
uspto-grants-2009_03
Patent number
US07501430B2

Reaction notes

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