Fumaric Acid → HCID 46910767, compound

HRID 2363690Notes

Reaction equation

HRID 2363690 reaction equation
[OH:1][CH2:2][C@H:3]([NH:7][C:8]1[N:13]=[C:12]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=3)=[CH:18][CH:17]=2)[N:11]2[N:28]=[CH:29][C:30]([CH:31]([CH3:33])[CH3:32])=[C:10]2[N:9]=1)[C@@H:4]([OH:6])[CH3:5].[C:34]([OH:41])(=[O:40])/[CH:35]=[CH:36]/[C:37]([OH:39])=[O:38]>CCO.CCOCC>[C:34]([OH:41])(=[O:40])/[CH:35]=[CH:36]/[C:37]([OH:39])=[O:38].[OH:1][CH2:2][C@H:3]([NH:7][C:8]1[N:13]=[C:12]([NH:14][CH2:15][C:16]2[CH:17]=[CH:18][C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=3)=[CH:20][CH:21]=2)[N:11]2[N:28]=[CH:29][C:30]([CH:31]([CH3:33])[CH3:32])=[C:10]2[N:9]=1)[C@@H:4]([OH:6])[CH3:5]

Participants

4

Reactant 2

HCID 444972Fumaric AcidHCID 46910766HCID 46910766, compound

Product 1

HCID 46910767HCID 46910767, compound

Reagents, catalysts & solvents 1

HCID 21585056Diethyl ether ethanolSolvent

Procedure

The product 14 is treated with fumaric acid in an EtOH/Et2O solution. The fumaric acid salt 15 crystallizes from the reaction medium. Mp=187-189° C. 1H NMR (300 MHz, DMSO-d6): δ 13.12 (bs, 2H, OH), 8.75 (bs, 1H, NH), 8.64 (d, 1H, J=4.5 Hz, Harom), 8.03 (d, 2H, J=8.1 Hz, Harom), 7.94-7.82 (m, 2H, Harom), 7.72 (s, 1H, Harom), 7.49 (bs, 2H, Harom) 7.35-7.31 (m, 1H, Harom), 6.62 (s, 2H, 2 ═CH), 6.05 (d, 1H, J=8.7 Hz, NH), 4.67 (bs, 2H, CH2), 4.00-3.89 (bs, 1H, CH), 3.89-3.76 (bs, 1H, CH), 3.58-3.40 (m, 2H, CH2), 2.90 (hept, 1H, J=7.0 Hz, CH), 1.22 (d, 6H, J=5.8 Hz, 2 CH3), 1.04 (bs, 3H, CH3).

Workup

  1. customThe fumaric acid salt 15 crystallizes from the reaction medium

Sources & evidence

ORD record
ord-7d164667b4b34971979270208f253720
Source dataset
uspto-grants-2014_04
Patent number
US08691982B2

Reaction notes

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