1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 117728727, compound

HRID 718681Notes

Reaction equation

HRID 718681 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[C:8]3[N:9]([C:13]([C:28]4[CH:29]=[CH:30][C:31]([C:34]([OH:36])=O)=NC=4)=[C:14]([C:16]#[C:17][C:18]4[CH:27]=[CH:26][C:25]5[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=5)[N:19]=4)[N:15]=3)[N:10]=[CH:11][CH:12]=2)[CH2:3][CH2:2]1.Cl.[CH3:38][NH:39][O:40][CH3:41].[CH3:42][CH2:43]N=C=NCCCN(C)C.CCN(C(C)C)C(C)C>C(Cl)Cl.CN(C=O)C.CCOC(C)=O>[CH3:41][O:40][N:39]([CH3:38])[C:34](=[O:36])[C:31]1[CH:30]=[CH:29][C:28]([C:13]2[N:9]3[N:10]=[CH:11][CH:12]=[C:7]([N:4]4[CH2:3][CH2:2][O:1][CH2:6][CH2:5]4)[C:8]3=[N:15][C:14]=2[C:16]#[C:17][C:18]2[CH:27]=[CH:26][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:19]=2)=[CH:43][CH:42]=1

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 117728384HCID 117728384, compound

Product 1

HCID 117728727HCID 117728727, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

A mixture of compound 40a (200 mg, 0.421 mmol), N,O-dimethylhydroxylamine hydrochloride (46.1 mg, 0.463 mmol), EDCI (88.7 mg, 0.463 mmol) and DIEA (87.0 μL, 0.505 mmol) in 12 mL of 2:1 DCM/DMF was stirred at rt for 16 h. The mixture was treated with 100 mL of EtOAc and washed with water (2×30 mL), brine (30 mL) and then dried over Na2SO4, filtered, and concentrated. The residue was purified by flash column chromatography on silica gel (0:1-1:1 EtOAc/DCM) to afford compound 65a as a pale yellow solid. 1H-NMR (CDCl3; 400 MHz) δ 8.33 (d, J=8.6 Hz, 2H), 8.07-8.21 (m, 5H), 7.83 (d, J=8.1 Hz, 1H), 7.75 (t, J=7.6 Hz, 1H), 7.53-7.65 (m, 2H), 6.16 (d, J=5.6 Hz, 1H), 4.05 (br. s., 4H), 3.89-4.00 (m, 4H), 2.66 (s, 3H). Mass spectrum (ESI, m/z): Calcd. for C29H23N5O2, 474.5 (M+H). found 474.2.

Workup

  1. washwashed with water (2×30 mL), brine (30 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by flash column chromatography on silica gel (0:1-1:1 EtOAc/DCM)

Sources & evidence

ORD record
ord-c4bc0114757541dc9a836da44b14e0f1
Source dataset
uspto-grants-2015_11
Patent number
US09193736B2

Reaction notes

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