Diisopropylethylamine → HCID 118235436, compound
Reaction equation
[F:1][CH:2]([F:36])[O:3][C:4]1[CH:35]=[CH:34][CH:33]=[CH:32][C:5]=1[CH2:6][C:7]1[N:11]2[CH:12]=[C:13]([C:16]3[CH:17]=[N:18][C:19]([N:22]4[CH2:27][CH2:26][CH:25]([C:28]([OH:30])=O)[CH2:24][CH2:23]4)=[N:20][CH:21]=3)[CH:14]=[CH:15][C:10]2=[N:9][C:8]=1[CH3:31].Cl.[CH3:38][O:39][NH2:40].Cl.C(N=C=NCCCN(C)C)C.CCN(C(C)C)C(C)C>CN(C=O)C.O>[F:1][CH:2]([F:36])[O:3][C:4]1[CH:35]=[CH:34][CH:33]=[CH:32][C:5]=1[CH2:6][C:7]1[N:11]2[CH:12]=[C:13]([C:16]3[CH:17]=[N:18][C:19]([N:22]4[CH2:23][CH2:24][CH:25]([C:28]([NH:40][O:39][CH3:38])=[O:30])[CH2:26][CH2:27]4)=[N:20][CH:21]=3)[CH:14]=[CH:15][C:10]2=[N:9][C:8]=1[CH3:31]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 50 °C
Procedure
A solution of Example 23 (0.108 g, 0.22 mmol), O-methylhydroxylamine hydrochloride (0.022 g, 0.26 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.053 g, 0.26 mmol) and DIPEA (0.057 g, 0.44 mmol) in DMF (5 mL) was stirred at r.t. for 18 h. Further O-methylhydroxylamine hydrochloride (0.10 g, 1.2 mmol) and DIPEA (300 μL) were added and the reaction mixture was heated at 50° C. for 2 days. The reaction mixture was cooled to r.t., treated with water (10 mL) and extracted with DCM (3×50 mL). The combined organic layers were concentrated in vacuo, and the resulting orange oil was purified by FCC (eluting with 3-10% MeOH in DCM), to give the title compound (4 mg, 3%) as an orange solid. HPLC-MS (pH 10): MH+ m/z 523.8 [M+H]+, RT 1.82 minutes.
Workup
- temperatureThe reaction mixture was cooled to r.t.
- extractionextracted with DCM (3×50 mL)
- concentrationThe combined organic layers were concentrated in vacuo
- customthe resulting orange oil was purified by FCC (eluting with 3-10% MeOH in DCM)
Sources & evidence
- ORD record
- ord-709cb0167fdf4f199d170fa7ac18feaf
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09309243B2
Reaction notes
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