Fumaric Acid → HCID 66758394, compound

HRID 393816Notes

Reaction equation

HRID 393816 reaction equation
[N:1]1([C:9]2[CH:10]=[N:11][CH:12]=[C:13]([CH:16]=2)[C:14]#[N:15])[CH2:5][CH2:4][C@H:3]2[CH2:6][NH:7][CH2:8][C@@H:2]12.[C:17]([OH:24])(=[O:23])/[CH:18]=[CH:19]/[C:20]([OH:22])=[O:21]>>[C:17]([OH:24])(=[O:23])/[CH:18]=[CH:19]/[C:20]([OH:22])=[O:21].[N:1]1([C:9]2[CH:10]=[N:11][CH:12]=[C:13]([CH:16]=2)[C:14]#[N:15])[CH2:5][CH2:4][C@H:3]2[CH2:6][NH:7][CH2:8][C@@H:2]12

Participants

3

Reactant 2

HCID 444972Fumaric AcidHCID 10013494HCID 10013494, compound

Product 1

HCID 66758394HCID 66758394, compoundYield 36%

Procedure

The crude product of Example 83B (4.29 mmol) and fumaric acid (0.501 g, 4.29 mmol) were processed according to the procedure described in Example 66D to provide the title compound (0.510 g, 1.54 mmol, 36% yield over two steps). 1H NMR (CH3OH-d4, 300 MHz) δ2.03 (m, 1H), 2.31 (m, 1H), 3.26 (m, 1H), 3.35 (m, 1H), 3.42 (dd, J=5.7, 4.0 Hz, 1H), 3.46 (m, 2H), 3.52 (dd, J=12.5, 5.7 Hz, 1H), 3.70 (dt, J=9.9, 6.8 Hz, 1H), 4.46 (m, 1H), 6.67 (s, 2H), 7.38 (dd, J=3.1, 1.7 Hz, 1H), 8.21 (d, J=3.1 Hz, 1H), 8.2 (d, J=1.7 Hz, 1H); MS (DCI/NH3) m/z 215 (M+H-C4H4O4)+; Anal. calculated for C12H14N4.C4H4O4: C, 58.17; H, 5.49; N, 16.96. Found: C, 58.17; H, 5.73; N, 17.32.

Sources & evidence

ORD record
ord-e23b3a6221134c4cae55a7ab7c8fefab
Source dataset
uspto-grants-2004_10
Patent number
US06809105B2

Reaction notes

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