Morpholine → HCID 76286072, compound

HRID 2170921Notes

Reaction equation

HRID 2170921 reaction equation
[CH:1]1([C:4]2[N:5]=[CH:6][N:7]([C:9]3[C:14](F)=[CH:13][N:12]=[C:11]([C:16]([NH:18][C:19]4[N:20]=[C:21]([C:24]5[N:28]([CH:29]6[CH2:31][CH2:30]6)[CH:27]=[N:26][N:25]=5)[S:22][CH:23]=4)=[O:17])[CH:10]=3)[CH:8]=2)[CH2:3][CH2:2]1.C([O-])([O-])=O.[K+].[K+].[NH:38]1[CH2:43][CH2:42][O:41][CH2:40][CH2:39]1>CN(C=O)C>[CH:1]1([C:4]2[N:5]=[CH:6][N:7]([C:9]3[C:14]([N:38]4[CH2:43][CH2:42][O:41][CH2:40][CH2:39]4)=[CH:13][N:12]=[C:11]([C:16]([NH:18][C:19]4[N:20]=[C:21]([C:24]5[N:28]([CH:29]6[CH2:31][CH2:30]6)[CH:27]=[N:26][N:25]=5)[S:22][CH:23]=4)=[O:17])[CH:10]=3)[CH:8]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 86723574HCID 86723574, compound

Product 1

HCID 76286072HCID 76286072, compoundYield 75.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of intermediate D (450 mg, 1.03 mmol) and K2CO3 (430 mg, 3.09 mmol) in DMF (3 mL) was added morpholine (270 μl, 3.09 mmol) and the reaction was heated to 80° C. overnight. The reaction was concentrated and purified by RP-HPLC to afford 390 mg (75% y) of 4-(4-cyclopropyl-1H-imidazol-1-yl)-N-(2-(4-cyclopropyl-4H-1,2,4-triazol-3-yl)thiazol-4-yl)-5-morpholinopicolinamide. All final compounds were isolated as the HCl salt from the preparative HPLC.

Workup

  1. concentrationThe reaction was concentrated
  2. custompurified by RP-HPLC

Sources & evidence

ORD record
ord-3e5fa72eab614d468aea64513838b8dc
Source dataset
uspto-grants-2015_06
Patent number
US09051313B2

Reaction notes

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