Morpholine → HCID 73294355, compound

HRID 1398053Notes

Reaction equation

HRID 1398053 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[C:13]([C:14]2[CH:22]=[CH:21][C:17]([C:18](Cl)=[O:19])=[CH:16][CH:15]=2)=[CH:12][C:11]([CH:23]2[CH2:28][C:27]([CH3:30])([CH3:29])[O:26][C:25]([CH3:32])([CH3:31])[CH2:24]2)=[N:10]1.[NH:33]1[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[C:13]([C:14]2[CH:22]=[CH:21][C:17]([C:18]([N:33]3[CH2:38][CH2:37][O:36][CH2:35][CH2:34]3)=[O:19])=[CH:16][CH:15]=2)=[CH:12][C:11]([CH:23]2[CH2:28][C:27]([CH3:30])([CH3:29])[O:26][C:25]([CH3:32])([CH3:31])[CH2:24]2)=[N:10]1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 73294181HCID 73294181, compound

Product 1

HCID 73294355HCID 73294355, compoundYield 80.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(1-(2-methoxyphenyl)-3-(2,2,6,6-tetramethyltetrahydro-2H-pyran-4-yl)-1H-pyrazol-5-yl)benzoyl chloride (28 mg, 0.062 mmol) in 0.62 mL of DCM at Rt was added morpholine (0.016 mL, 0.19 mmol) and the mixture stirred for 10 mins. The solvents were evaporated and the crude product purified by RP-HPLC, eluting with a linear gradient of 30-70% CH3CN in 0.1% TFA/H2O over 10 mins to give 25 mg (69%) of the title compound as white solid containing 0.6 eq of TFA.

Workup

  1. customThe solvents were evaporated
  2. customthe crude product purified by RP-HPLC
  3. washeluting with a linear gradient of 30-70% CH3CN in 0.1% TFA/H2O over 10 mins

Sources & evidence

ORD record
ord-3191edf67e2e4200b8859c83e7319171
Source dataset
uspto-grants-2014_12
Patent number
US08901314B2

Reaction notes

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