Fumaric Acid → HCID 86584386, compound

HRID 1817019Notes

Reaction equation

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

Participants

Reactant 2

HCID 444972Fumaric Acid

HCID 10466175HCID 10466175, compound

Product 1

HCID 86584386HCID 86584386, compoundYield 79%

Procedure

The product of Example 77D (0.260 g, 1.16 mmol) and fumaric acid (0.135 g, 1.16 mmol) were processed according to the procedure described in Example 66D to provide the title compound (0.310 g, 0.912 mmol, 79% yield). 1H NMR (CH3OH-d4, 500 MHz) δ 2.00 (m, 1H), 2.30 (m, 1H), 3.32 (m, 4H), 3.50 (dt, J=12.5, 5.9 Hz, 2H), 3.67 (dt, J=9.7, 6.3 Hz, 1H), 4.39 (m, 1H), 6.67 (s, 2H), 7.12 (dd, J=8.8, 3.1 Hz, 1H) 7.27 (d, J=8.8 Hz, 1H), 7.73 (d, J=3.1 Hz, 1H); MS (DCI/NH3) m/z 224 (M+H−C4H4O4)+; Anal. calculated for C11H14ClN3.C4H4O4: C, 53.02; H, 5.34; N, 12.37. Found: C, 52.86; H, 5.31; N, 12.30.

Sources & evidence

ORD record: ord-c73b5bc1aa8f41809d931771a7c88ea6
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07598236B2

Reaction notes

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