Dimethylformamide → HCID 57516319, compound
Reaction equation
[C:1]([NH:8][CH2:9][C:10]([OH:12])=O)([O:3]C(C)(C)C)=O.[C:13]([C:20]1NC=CN=1)([C:15]1NC=CN=1)=O.[N:25]1([C:31]2[CH:45]=[CH:44][CH:43]=[CH:42][C:32]=2[C:33]([NH:35][C:36]2[CH:37]=[N:38][CH:39]=[CH:40][CH:41]=2)=[O:34])[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1.C(N([CH2:51][CH3:52])CC)C.[CH3:53]N(C=O)C>C(OCC)(=O)C>[C:1]([NH:8][CH2:9][C:10]([N:28]1[CH2:29][CH2:30][N:25]([C:31]2[CH:45]=[CH:44][CH:43]=[CH:42][C:32]=2[C:33]([NH:35][C:36]2[CH:37]=[N:38][CH:39]=[CH:40][CH:41]=2)=[O:34])[CH2:26][CH2:27]1)=[O:12])(=[O:3])[C:15]1[CH:13]=[CH:20][CH:52]=[CH:51][CH:53]=1Participants
7
Procedure
A solution of N-Boc-glycine (106 mg, 0.591 mmol) and carbonyl diimidazole (98 mg, 0.59 mmol) in DMF (10 mL) is stirred at room temperature for 60 min. To the solution is added 2-piperazin-1-yl-N-pyridin-3-yl-benzamide (200 mg, 0.563 mmol) and triethylamine (0.394 mL, 2.82 mmol) and the solution is stirred at room temperature for 24 h. The reaction is diluted ethyl acetate (100 mL) and washed with saturated NaHCO3 (100 mL), 50% sat. NH4Cl (100 mL), then water (100 mL). The aqueous layers are extracted again with more ethyl acetate (100 mL). The organics are dried (Na2SO4) and concentrated and dried to give 0.241 g of the desired amide intermediate in 93% yield as a gum.
Workup
- washwashed with saturated NaHCO3 (100 mL), 50% sat. NH4Cl (100 mL)
- extractionThe aqueous layers are extracted again with more ethyl acetate (100 mL)
- dry with materialThe organics are dried (Na2SO4)
- concentrationconcentrated
- customdried
Sources & evidence
- ORD record
- ord-2f57db9170c64d449197a116f311a8c4
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08362249B2
Reaction notes
Loading…