Morpholine → HCID 86594956, compound

HRID 1435698Notes

Reaction equation

HRID 1435698 reaction equation
N1CCOCC1.Cl.Cl.[N:9]1([CH2:15][C:16]2[N:17]=[C:18]([NH2:21])[S:19][CH:20]=2)[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1.[Cl:22][C:23]1[C:24]([CH3:33])=[C:25]([S:29](Cl)(=[O:31])=[O:30])[CH:26]=[CH:27][CH:28]=1>>[ClH:22].[Cl:22][C:23]1[C:24]([CH3:33])=[C:25]([S:29]([NH:21][C:18]2[S:19][CH:20]=[C:16]([CH2:15][N:9]3[CH2:14][CH2:13][O:12][CH2:11][CH2:10]3)[N:17]=2)(=[O:31])=[O:30])[CH:26]=[CH:27][CH:28]=1

Participants

4

Reactant 3

HCID 8083Morpholine2×HCID 5227343-Chloro-2-methylbenzenesulfonyl chlorideHCID 86594958HCID 86594958, compound

Product 1

HCID 86594956HCID 86594956, compoundYield 6%

Procedure

A mixture of INTERMEDIATE 19 (0.50 g, 2.70 mmol) and morpholine (1.65 g, 18.92 mmol) was stirred at room temperature over night. The solvent was evaporated and the solid residue was purified by reversed phase flash chromatography on LiChroprep RP-18. The product was eluting with (1% CH3CN in H2O/0.5% conc. HCl) giving approximately a 1:1 mixture of 4-(4-morpholinylmethyl)-1,3-thiazol-2-amine dihydrochloride and morpholine (1.33 g). This material was sulphonylated with 3-chloro-2-methylbenzenesulphonyl chloride according to the preparation as described for EXAMPLE 205A giving 17 mg (6%) of a solid: 1H NMR (DMSO) δ 2.65 (s, 3H), 3.08 (br m, 4H), 3.78 (br m, 4H), 4.13 (br s, 2H), 7.07 (s, 1H), 7.40 (t, 1H), 7.68 (d, 1H), 7.91 (d, 1H); MS (Ionspray, [M+H]+) m/z 387.

Workup

  1. customThe solvent was evaporated
  2. customthe solid residue was purified by reversed phase flash chromatography on LiChroprep RP-18
  3. washThe product was eluting with (1% CH3CN in H2O/0.5% conc. HCl)
  4. customgiving approximately

Sources & evidence

ORD record
ord-f8c216abc7334669a34eaab4de04ca88
Source dataset
uspto-grants-2009_11
Patent number
US07618961B2

Reaction notes

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