1,1'-Carbonyldiimidazole → HCID 54582481, compound
Reaction equation
[C:1]([C:5]1[N:6]=[C:7]([NH2:10])[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[C:11](N1C=CN=C1)(N1C=CN=C1)=[O:12].[N:23]1([C:30]([CH:32]2[CH2:37][CH2:36][O:35][CH2:34][CH2:33]2)=[O:31])[CH2:29][CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1>C(Cl)Cl>[C:1]([C:5]1[N:6]=[C:7]([NH:10][C:11]([N:26]2[CH2:27][CH2:28][CH2:29][N:23]([C:30]([CH:32]3[CH2:37][CH2:36][O:35][CH2:34][CH2:33]3)=[O:31])[CH2:24][CH2:25]2)=[O:12])[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2]Participants
Procedure
To a solution of 62.8 mg (0.4 mmol) of 4-tert-butyl-thiazol-2-ylamine in DCM (2 mL) were added 98 mg (0.6 mmol) of 1,1′-carbonyldiimidazole and the reaction was stirred for 4 h at room temperature. A solution of 354 mg (0.8 mmol) of [1,4]diazepan-1-yl-(tetrahydro-pyran-4-yl)-methanone (triple trifluoroacetic acid salt, prepared according to Method L, above) in DCM (3 mL) was added and the reaction stirred for 18 h at room temperature. The reaction mixture was washed with 10% aqueous citric acid solution (5 mL). The organic layer was dried over Na2SO4, filtered and the filtrate was concentrated under reduced pressure. The crude product was purified by mass-triggered preparative LCMS to afford 27.6 mg of 4-(tetrahydro-pyran-4-carbonyl)-[1,4]diazepane-1-carboxylic acid (4-tert-butyl-thiazol-2-yl)-amide.
Workup
- stirringthe reaction stirred for 18 h at room temperature
- washThe reaction mixture was washed with 10% aqueous citric acid solution (5 mL)
- dry with materialThe organic layer was dried over Na2SO4
- filtrationfiltered
- concentrationthe filtrate was concentrated under reduced pressure
- customThe crude product was purified by mass-triggered preparative LCMS
Sources & evidence
- ORD record
- ord-cf70d1365d5a4f7aa964bb7c96c0f046
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08173638B2
Reaction notes
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