Triethylamine → HCID 58514868, compound

HRID 449276Notes

Reaction equation

HRID 449276 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([CH2:11][N:12]3[C:16]4=[N:17][C:18]([C:21]5[CH:29]=[CH:28][C:24]([C:25]([OH:27])=O)=[CH:23][CH:22]=5)=[CH:19][CH:20]=[C:15]4[N:14]=[N:13]3)=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)CC)C.[N:64]1([CH:69]2[CH2:74][CH2:73][NH:72][CH2:71][CH2:70]2)[CH2:68][CH2:67][CH2:66][CH2:65]1>O.CN(C=O)C.ClCCl>[N:64]1([CH:69]2[CH2:74][CH2:73][N:72]([C:25]([C:24]3[CH:28]=[CH:29][C:21]([C:18]4[N:17]=[C:16]5[N:12]([CH2:11][C:7]6[CH:6]=[C:5]7[C:10](=[CH:9][CH:8]=6)[N:1]=[CH:2][CH:3]=[CH:4]7)[N:13]=[N:14][C:15]5=[CH:20][CH:19]=4)=[CH:22][CH:23]=3)=[O:27])[CH2:71][CH2:70]2)[CH2:68][CH2:67][CH2:66][CH2:65]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 787034-(1-Pyrrolidinyl)piperidineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 54670137HCID 54670137, compound

Product 1

HCID 58514868HCID 58514868, compoundYield 12.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

To a solution of example 8 (0.100 g, 0.262 mmol) in 1:1 DMF/dichloromethane mixture (1.0 ml), BOP (0.121 g, 0.275 mmol) and triethylamine (0.1 ml, 0.786 mmol) were added and stirred for 30 min. 4-(pyrrolidin-1-yl)piperidine (0.044 g, 0.288 mmol) was added at RT and the reaction mixture was stirred for 12 h. To the reaction mixture water was added and extracted with ethyl acetate, dried over sodium sulphate and concentrated under reduced pressure. The crude product was purified by column chromatography with methanol:dichloromethane to afford the title compound as a yellow solid (0.017 g, 12%). M.P.: 125-127° C. 1H-NMR (δ ppm, DMSO-d6, 400 MHz): 8.88 (dd, J=4.2, 1.6 Hz, 1H), 8.71 (d, J=8.7 Hz, 1H), 8.38 (d, J=8.1 Hz, 1H), 8.33 (d, J=8.2 Hz, 2H), 8.19 (d, J=8.8 Hz, 1H), 8.03 (d, J=8.9 Hz, 1H), 8.00 (s, 1H), 7.83 (dd, J=8.7, 1.9 Hz, 1H), 7.57 (d, J=8.2 Hz, 2H), 7.53 (dd, J=8.4, 4.2 Hz, 1H), 6.22 (s, 2H), 3.49-3.10 (m, 9H), 2.07-1.53 (m, 8H).

Workup

  1. stirringthe reaction mixture was stirred for 12 h
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by column chromatography with methanol

Sources & evidence

ORD record
ord-b9f0dd7c64f44cdcbd893e3f766da393
Source dataset
uspto-grants-2013_07
Patent number
US08481739B2

Reaction notes

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