4-Methylmorpholine → HCID 59352423, compound

HRID 1407905Notes

Reaction equation

HRID 1407905 reaction equation
[CH3:1][C:2]1[C:6]2[CH:7]=[C:8]3[C:13]4([C:21]5[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=5)[N:15]([CH2:22][C:23]5[O:24][CH:25]=[C:26]([C:28]([OH:30])=O)[N:27]=5)[C:14]4=[O:31])[CH2:12][O:11][C:9]3=[CH:10][C:5]=2[O:4][N:3]=1.Cl.[CH3:33][NH:34][CH3:35].O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.CN1CCOCC1>CN(C)C=O>[CH3:33][N:34]([CH3:35])[C:28]([C:26]1[N:27]=[C:23]([CH2:22][N:15]2[C:16]3[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:13]3([C:8]4[C:9](=[CH:10][C:5]5[O:4][N:3]=[C:2]([CH3:1])[C:6]=5[CH:7]=4)[O:11][CH2:12]3)[C:14]2=[O:31])[O:24][CH:25]=1)=[O:30]

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 10473Dimethylamine, hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 59352379HCID 59352379, compound

Product 1

HCID 59352423HCID 59352423, compoundYield 68.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-[(3-methyl-2′-oxospiro[furo[3,2-f][1,2]benzisoxazole-5,3′-indol]-1′(2′H)-yl)methyl]-1,3-oxazole-4-carboxylic acid (0.32 g, 0.76 mmol), dimethylamine hydrochloride (0.13 g, 1.52 mmol), 1-hydroxybenzotriazole hydrate (0.16 g, 1.17 mmol), 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (0.21 g, 1.07 mmol), 4-methylmorpholine (0.23 mL, 2.07 mmol) and anhydrous N,N-dimethylformamide (10 mL) was stirred at ambient temperature for 16 h. The reaction mixture was concentrated in vacuo, and the residue recrystallized from diethyl ether to afford N,N-dimethyl-2-[(3-methyl-2′-oxospiro[furo[3,2-f][1,2]benzisoxazole-5,3′-indol]-1′(2′H)-yl)methyl]-1,3-oxazole-4-carboxamide (0.23 g, 68%) as a colorless solid: mp 87-89° C. (diethyl ether); 1H NMR (300 MHz, CDCl3) δ 8.10 (s, 1H), 7.48-7.5 (m, 1H), 7.31-7.25 (m, 1H), 7.14-7.11 (m, 1H), 7.05-6.95 (m, 3H), 5.28-5.06 (m, 3H), 4.87-4.84 (m, 1H), 3.32 (s, 3H), 3.06 (s, 3H), 2.43 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 175.8, 164.0, 161.7, 158.2, 157.1, 154.9, 143.7, 141.3, 137.2, 130.1, 129.5, 124.0, 123.9, 123.2, 118.0, 109.3, 108.6, 107.9, 81.3, 56.3, 38.4, 37.5, 36.2, 9.8; MS (ES+) m/z 444.8 (M+1).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue recrystallized from diethyl ether

Sources & evidence

ORD record
ord-913f01e8ec224b7cbfcb3a70835db4b7
Source dataset
uspto-grants-2014_12
Patent number
US08916580B2

Reaction notes

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