Fumaric Acid → HCID 86584386, compound

HRID 1642189Notes

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-a5c83af71ea348ac872146b4940aa2a0
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08119635B2

Reaction notes

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