4-Methylmorpholine → HCID 57721191, compound

HRID 1986401Notes

Reaction equation

HRID 1986401 reaction equation
[NH2:1][C:2]1[C:3]([C:7]2[N:8]([CH2:26][CH3:27])[C:9]3[CH:14]=[C:13]([CH2:15][C:16]4[CH:17]=[C:18]([CH:22]=[CH:23][CH:24]=4)[C:19]([OH:21])=O)[N:12]=[CH:11][C:10]=3[N:25]=2)=[N:4][O:5][N:6]=1.[N:28]1([CH2:34][CH2:35][NH2:36])[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1.C1C=CC2N(O)N=NC=2C=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN1CCOCC1>CN(C=O)C>[NH2:1][C:2]1[C:3]([C:7]2[N:8]([CH2:26][CH3:27])[C:9]3[CH:14]=[C:13]([CH2:15][C:16]4[CH:17]=[C:18]([CH:22]=[CH:23][CH:24]=4)[C:19]([NH:36][CH2:35][CH2:34][N:28]4[CH2:33][CH2:32][O:31][CH2:30][CH2:29]4)=[O:21])[N:12]=[CH:11][C:10]=3[N:25]=2)=[N:4][O:5][N:6]=1

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 4082852-MorpholinoethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68872394HCID 68872394, compound

Product 1

HCID 57721191HCID 57721191, compoundYield 130.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under nitrogen, to a solution of the product of Step 2 (31 mg, 85 μmol) in DMF (2 mL), was added [2-(4-morpholinyl)ethyl]amine (23 mg, 170 mmol), HOBT (35 mg, 0.26 mmol), HBTU (49 mg, 0.13 mmol), followed with 4-methylmorpholine (30 μL, 0.26 mmol). This mixture was then stirred at rt for overnight. The reaction mixture was concentrated, residue was purified with reverse phase HPLC (10% MeCN/H2O→80% MeCN/H2O, containing 0.1% TFA), to afford the title compound as a pale yellow solid (53 mg, 90%). %). 1H NMR (400 MHz, DMSO) δ ppm 9.74 (t, 1H, 4.4 Hz), 9.28 (s, 1H), 8.73 (t, 1H, 5.2 Hz), 8.16 (s, 1H), 7.87 (s, 1H), 7.73 (d, 1H, 8.0 Hz), 7.56 (d, 1H, 7.2 Hz), 7.49 (d, 1H, 7.6 Hz), 6.96 (s, 2H), 4.72 (q, 2H, 7.2 Hz), 4.41 (s, 2H), 4.00 (d, 2H, 11.2 Hz), 3.53-3.68 (m, 6H), 3.30 (bs, 2H), 3.14-3.17 (m, 2H), 1.42 (t, 3H, 7.2 Hz). MS (ES+) m/e 477 [M+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customresidue was purified with reverse phase HPLC (10% MeCN/H2O→80% MeCN/H2O, containing 0.1% TFA)

Sources & evidence

ORD record
ord-2e0f02b9dd0c4b098cdbd9b47f026b5d
Source dataset
uspto-grants-2009_06
Patent number
US07547779B2

Reaction notes

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