Diisopropylethylamine → HCID 67187460, compound

HRID 885974

Reaction equation

HRID 885974 reaction equation
[NH2:1][C:2]1[CH:23]=[CH:22][C:5]2[N:6]([C:10]3[S:11][C:12]4[C:13](=[O:21])[NH:14][C:15]([CH3:20])([CH3:19])[CH2:16][C:17]=4[N:18]=3)[CH2:7][CH2:8][O:9][C:4]=2[CH:3]=1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.Cl.[CH3:49][N:50]1[CH2:55][CH2:54][CH:53]([C:56](O)=[O:57])[CH2:52][CH2:51]1.CCN(C(C)C)C(C)C>CN(C=O)C.O.CC#N>[CH3:19][C:15]1([CH3:20])[NH:14][C:13](=[O:21])[C:12]2[S:11][C:10]([N:6]3[C:5]4[CH:22]=[CH:23][C:2]([NH:1][C:56]([CH:53]5[CH2:54][CH2:55][N:50]([CH3:49])[CH2:51][CH2:52]5)=[O:57])=[CH:3][C:4]=4[O:9][CH2:8][CH2:7]3)=[N:18][C:17]=2[CH2:16]1

Participants

8

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 27600434-Piperidinecarboxylic acid, 1-methyl-, hydrochloride (1:1)HCID 67185695HCID 67185695, compound

Product 1

HCID 67187460HCID 67187460, compoundYield 51.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of Example 233 (0.049 g, 0.15 mmol), 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (0.111 g, 0.29 mmol) and 1-methylpiperidine-4-carboxylic acid hydrochloride (0.034 g, 0.19 mmol) in DMF (0.5 mL) was added DIPEA (0.06 mL, 0.35 mmol). The reaction mixture was stirred at r.t. for 16 h. MeCN (1 mL) and water (1 mL) were added. The insoluble material was filtered, and the filtrate concentrated in vacuo. Purification by preparative HPLC (Method 6) gave the title compound (0.035 g, 51%) as a yellow solid. δH (CD3OD) 7.91 (1H, d, J 9.0 Hz), 7.37 (1H, d, J 2.3 Hz), 7.11 (1H, dd, J 8.9 and 2.3 Hz), 4.40-4.30 (2H, m), 4.20-4.09 (2H, m), 3.62 (2H, d, J 12.6 Hz), 3.17-3.02 (2H, m), 2.92 (3H, s), 2.89 (2H, s), 2.76-2.60 (1H, m), 2.34-1.91 (4H, m), 1.39 (6H, s). Exchangeable protons were not observed. LCMS (ES+) 456.21 (M+H)+, RT 1.80 minutes (Method 1).

Workup

  1. filtrationThe insoluble material was filtered
  2. concentrationthe filtrate concentrated in vacuo
  3. customPurification by preparative HPLC (Method 6)

Sources & evidence

ORD record
ord-fcbfc1827857424ba3909b4ecdeac4af
Source dataset
uspto-grants-2012_08
Patent number
US08242116B2

Linked notes

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