[(1S,2S,4S)-Bicyclo[2.2.1]hept-5-en-2-yl]acetic acid → HCID 67160315, compound

HRID 469626Notes

Reaction equation

HRID 469626 reaction equation
[NH2:1][N:2]1[N:11]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:19].[C@@H:20]12[CH2:26][C@@H:23]([CH:24]=[CH:25]1)[CH2:22][C@H:21]2[CH2:27][C:28](O)=[O:29]>>[C@@H:20]12[CH2:26][C@@H:23]([CH:24]=[CH:25]1)[CH2:22][C@H:21]2[CH2:27][C:28]([NH:1][N:2]1[N:11]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:19])=[O:29]

Participants

3

Reactant 2

HCID 28063363[(1S,2S,4S)-Bicyclo[2.2.1]hept-5-en-2-yl]acetic acidHCID 67160399HCID 67160399, compound

Product 1

HCID 67160315HCID 67160315, compound

Procedure

The product of Example 129A and 2-[(1S,2S,4S)-bicyclo[2.2.1]hept-5-en-2-yl]acetic acid were treated using a method similar to that described in Example 17C to give the title compound. 1H NMR (400 MHz, DMSO-d6) δ 11.29 (s, 1H), 8.43-8.37 (m, 1H), 8.05-7.88 (m, 2H), 7.76-7.68 (m, 1H), 7.70-7.61 (m, 2H), 7.48-7.34 (m, 2H), 6.22 (dd, J=5.7, 2.9, 1H), 6.06 (dd, J=5.7, 2.8, 1H), 2.92-2.86 (m, 1H), 2.81-2.75 (m, 1H), 2.42-2.48 (m, buried), 2.19-1.98 (m, 2H), 1.90 (ddd, J=11.6, 9.0, 3.8, 1H), 1.39-1.30 (m, 1H), 1.30-1.22 (m, 1H), 0.60 (ddd, J=11.6, 4.2, 2.6, 1H); MS (APCI+) M/Z 390 (M+H)+.

Sources & evidence

ORD record
ord-c579d68adce84973aceead12dad60adf
Source dataset
uspto-grants-2014_01
Patent number
US08629143B2

Reaction notes

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