Morpholine → HCID 68380159, compound

HRID 573657Notes

Reaction equation

HRID 573657 reaction equation
CS(O[CH2:6][C:7]#[C:8][C:9]1[S:29][C:12]2=[N:13][C:14]([CH3:28])=[CH:15][C:16]([NH:17][S:18]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=3)(=[O:20])=[O:19])=[C:11]2[C:10]=1[C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([O:36][CH3:37])[CH:31]=1)(=O)=O.[NH:38]1[CH2:43][CH2:42][O:41][CH2:40][CH2:39]1>C1COCC1>[Cl:27][C:23]1[CH:22]=[C:21]([S:18]([NH:17][C:16]2[CH:15]=[C:14]([CH3:28])[N:13]=[C:12]3[S:29][C:9]([C:8]#[C:7][CH2:6][N:38]4[CH2:43][CH2:42][O:41][CH2:40][CH2:39]4)=[C:10]([C:30]4[CH:35]=[CH:34][CH:33]=[C:32]([O:36][CH3:37])[CH:31]=4)[C:11]=23)(=[O:20])=[O:19])[CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 86671852HCID 86671852, compound

Product 1

HCID 68380159HCID 68380159, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 3-{4-{[(3-chlorophenyl)sulfonyl]amino}-6-methyl-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridin-2-yl}-2-propyn-1-yl methanesulfonate (Description 77) (14 mg, 0.024 mmol) and morpholine (21.14 μl, 0.243 mmol) in THF (221 μl) was stirred at 60° C. for 1 h. The mixture was evaporated to dryness and the residue purified on silica, eluting with a gradient of 0-10% 2M NH3 in MeOH in DCM, to afford the title compound (12 mg). LCMS (A) m/z: 568 [M+1]+, Rt 1.02 min (acidic).

Workup

  1. customThe mixture was evaporated to dryness
  2. customthe residue purified on silica
  3. washeluting with a gradient of 0-10% 2M NH3 in MeOH in DCM

Sources & evidence

ORD record
ord-2166d5bb1e3945068a0579771acc4aeb
Source dataset
uspto-grants-2015_05
Patent number
US09029545B2

Reaction notes

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