Fumaric Acid → HCID 178434232, compound

HRID 1441421Notes

Reaction equation

HRID 1441421 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]3[N:16]=[N:15][C:14]([O:17][C@@H:18]4[CH:23]5[CH2:24][CH2:25][N:20]([CH2:21][CH2:22]5)[CH2:19]4)=[CH:13][CH:12]=3)[CH:9]=2)[NH:4][N:3]=1.[C:26]([OH:33])(=[O:32])/[CH:27]=[CH:28]/[C:29]([OH:31])=[O:30]>CCOC(C)=O.CO>[C:26]([OH:33])(=[O:32])/[CH:27]=[CH:28]/[C:29]([OH:31])=[O:30].[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]3[N:16]=[N:15][C:14]([O:17][C@@H:18]4[CH:23]5[CH2:22][CH2:21][N:20]([CH2:25][CH2:24]5)[CH2:19]4)=[CH:13][CH:12]=3)[CH:9]=2)[NH:4][N:3]=1

Participants

4

Reactant 2

HCID 444972Fumaric AcidHCID 178434231HCID 178434231, compound

Product 1

HCID 178434232HCID 178434232, compoundYield 119%

Reagents, catalysts & solvents 1

HCID 21584119Ethylacetate methanolSolvent

Procedure

The product of Example 20B (68 mg, 0.11 mmol) was treated with fumaric acid (Aldrich, 14 mg, 0.12 mmol) in EtOAc/MeOH (v.10:1, 5 mL) to provide the title compound as solid (59.1 mg, 65%). 1H NMR (MeOH-D4, 300 MHz) 1.82-2.18 (m, 3H) 2.27-2.42 (m, 1H) 2.55-2.66 (m, 4H) 3.21-3.43 (m, 5H) 3.82-3.95 (m, 1H) 5.47-5.57 (m, 1H) 6.68 (s, 2H) 7.34 (d, J=9.2 Hz, 1H) 7.60 (d, J=8.8 Hz, 1H) 8.06 (dd, J=8.8, 1.7 Hz, 1H) 8.21 (d, J=9.2 Hz, 1H) 8.32 (s, 1H) ppm. MS (DCI/NH3) m/z 336(M+H)+. Anal. Calculated for C19H21N5O.1.0 C4H4O4.0.35 H2O: C, 60.35; H, 5.66; N, 15.30. Found: C, 60.06; H, 5.40; N, 15.56.

Sources & evidence

ORD record
ord-5d988d2fc70540c4ae429ae8dd03300c
Source dataset
uspto-grants-2010_02
Patent number
US07655657B2

Reaction notes

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