Dichloromethane → HCID 9828829, compound

HRID 442766Notes

Reaction equation

HRID 442766 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[O:10][C:11]1[CH:12]=[C:13]([C@@H:19]([C:27]2[CH:33]=[CH:32][C:30]([NH2:31])=[CH:29][CH:28]=2)[CH2:20][C:21]2[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=2)[CH:14]=[CH:15][C:16]=1[O:17][CH3:18].[CH2:34]([N:36]=[C:37]=[O:38])[CH3:35].C(OCC)(=O)C.[Cl:45]CCl>CN(C1C=CN=CC=1)C>[ClH:45].[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[O:10][C:11]1[CH:12]=[C:13]([C@@H:19]([C:27]2[CH:33]=[CH:32][C:30]([NH:31][C:37]([NH:36][CH2:34][CH3:35])=[O:38])=[CH:29][CH:28]=2)[CH2:20][C:21]2[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=2)[CH:14]=[CH:15][C:16]=1[O:17][CH3:18]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8022Ethyl isocyanateHCID 8857Ethyl AcetateHCID 15341166HCID 15341166, compound

Product 1

HCID 9828829HCID 9828829, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

To a solution of the aniline of Example 1 (50 mg, 1.15 mmol) in dichloromethane (5 ml) at RT was added DMAP (cat.) and ethyl isocyanate (100 μl, 1.1 eq) and the mixture stirred at this temperature overnight. The reaction mixture was concentrated in vacuo to yield a yellow foam, which was subjected to column chromatography (SiO2 ; ethyl acetate) to afford the free base of the title compound (445 mg, 77%) as a white foam. The material was converted to its hydrochloride salt (Found: C, 68.89, H, 6.38; N, 7.81. C32H33N3O3. HCl. 0.75 H2O requires C, 68.93; H, 6.42; N, 7.54%). δH (d4MeOH) 1.12 (3H, m), 2.96-3.30 (8H, m), 3.71 (3H, s), 4.36 (1H, t, J 8.0 Hz), 5.13 (1H, m), 6.87 (4H, m), 7.02 (1H, d, J 7.5 Hz), 7.11-7.16 (5H, m), 7.52 (1H, s), 7.83 (2H, br), and 8.58 (2H, br). m/z ESI 508 (MH+, 100%), 530 (MNa+, 3).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customto yield a yellow foam, which

Sources & evidence

ORD record
ord-d4829815e0b3403d84a8775f1b9a3281
Source dataset
uspto-grants-1999_04
Patent number
US05891896

Reaction notes

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