Fumaric Acid → HCID 86584387, compound

HRID 1642201Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[CH:6][C:5]([N:8]2[C@H:15]3[C@H:10]([CH2:11][CH2:12][NH:13][CH2:14]3)[CH2:9]2)=[CH:4][C:3]=1[CH3:16].[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].[Cl:1][C:2]1[N:7]=[CH:6][C:5]([N:8]2[C@H:15]3[C@H:10]([CH2:11][CH2:12][NH:13][CH2:14]3)[CH2:9]2)=[CH:4][C:3]=1[CH3:16]

Participants

Reactant 2

HCID 444972Fumaric Acid

HCID 9834620HCID 9834620, compound

Product 1

HCID 86584387HCID 86584387, compoundYield 70%

Procedure

The product of Example 89B (0.850 g, 0.359 mmol) and fumaric acid (42 mg, 0.359 mmol) were processed according to the procedure described in Example 66D to provide the title compound (97 mg, 0.250 mmol, 70% yield). 1H NMR(CH3OH-d4, 300 MHz) δ 2.05 (m, 1H), 2.30 (m, 1H), 2.32 (s, 3H), 2.85 (m, 1H), 3.15 (ddd, J=12.5, 8.1, 4.4 Hz, 1H), 3.31 (m, 1H), 3.57 (ddd, J=12.5, 8.5, 4.1 Hz, 1H), 3.64 (dd, J=14.6, 2.0 Hz, 1H), 3.77 (dd, J=7.1, 2.3 Hz, 1H), 3.83 (t, J=7.4 Hz, 1H), 4.34 (dt, J=7.8, 2.3 Hz, 1H), 6.69 (s, 2H), 7.04 (d, J=2.8 Hz, 1H), 7.57 (d, J=2.8 Hz, 1H); MS (DCI/NH3) m/z 238 (M+H−C4H4O4)+; Anal. calculated for C12H16ClN3.1.3C4H4O4: C, 53.16; H, 5.50; N, 10.81. Found: C, 52.91; H, 5.62; N, 10.86.

Sources & evidence

ORD record: ord-287557619d2746dab68937a3eb70d1bc
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08119635B2

Reaction notes

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