N,N-Dimethylglycine → 2-Dimethylamino-N-[2-((R)-indan-1-ylamino)-quinolin-5-yl]-acetamide
Reaction equation
[CH3:1][N:2]([CH3:7])[CH2:3][C:4](O)=[O:5].C(N(C(C)C)C(C)C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[C@H:39]1([NH:48][C:49]2[CH:58]=[CH:57][C:56]3[C:55]([NH2:59])=[CH:54][CH:53]=[CH:52][C:51]=3[N:50]=2)[C:47]2[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=2)[CH2:41][CH2:40]1.C([O-])(O)=O.[Na+]>ClCCl.CN(C=O)C>[CH3:1][N:2]([CH3:7])[CH2:3][C:4]([NH:59][C:55]1[CH:54]=[CH:53][CH:52]=[C:51]2[C:56]=1[CH:57]=[CH:58][C:49]([NH:48][C@H:39]1[C:47]3[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=3)[CH2:41][CH2:40]1)=[N:50]2)=[O:5]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Procedure
To a stirred solution of N,N-dimethylglycine (124 mg, 1.2 mmol) in dichloromethane (20 ml) and DMF (10 ml) were added at room temperature N-ethyldiisopropylamine (452 mg, 3.5 mmol) and TBTU (514 mg, 1.6 mmol) and the mixture was allowed to stir for 90 min. (R)—N2-indan-1-yl-quinoline-2,5-diamine (example 16) (275 mg, 1.0 mmol) was added and the reaction mixture was allowed to stir for 17 h, poured into sat. NaHCO3 solution (30 ml) and extracted with dichloromethane (2×30 ml). The combined organic layers were washed with water (30 ml), dried (MgSO4) and evaporated. The crude product was further purified by flash chromatography on silica gel (heptane/ethyl acetate) and crystallization (ethyl acetate/heptane) to yield the title compound as white solid (210 mg, 58%). M.p. 153° C.; MS: m/e=361.2 (M+H+).
Workup
- additionwas added
- extractionextracted with dichloromethane (2×30 ml)
- washThe combined organic layers were washed with water (30 ml)
- dry with materialdried (MgSO4)
- customevaporated
- customThe crude product was further purified by flash chromatography on silica gel (heptane/ethyl acetate) and crystallization (ethyl acetate/heptane)
Sources & evidence
- ORD record
- ord-4914b469b81f45018743d5e59e6502c5
- Source dataset
- uspto-grants-2011_08
- Patent number
- US07994324B2
Reaction notes
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