[(1S,2S,4S)-Bicyclo[2.2.1]hept-5-en-2-yl]acetic acid → HCID 67161451, compound

HRID 469640Notes

Reaction equation

[NH2:1][N:2]1[N:11]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:22].[C@@H:23]12[CH2:29][C@@H:26]([CH:27]=[CH:28]1)[CH2:25][C@H:24]2[CH2:30][C:31](O)=[O:32].[H][H]>>[C@@H:23]12[CH2:29][C@@H:26]([CH2:27][CH2:28]1)[CH2:25][C@H:24]2[CH2:30][C:31]([NH:1][N:2]1[N:11]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:19])[F:20])=[CH:14][CH:13]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:22])=[O:32]

Participants

Reactant 3

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

HCID 67160581HCID 67160581, compound

HCID 178418361HCID 178418361, compound

Product 1

HCID 67161451HCID 67161451, compound

Procedure

The product of Example 147A 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, followed by treatment with hydrogen similar to that described in Example 66 to give the title compound. 1H NMR (400 MHz, DMSO) δ 11.41-11.35 (m, 1H), 8.45-8.38 (m, 1H), 8.01-7.91 (m, 4H), 7.88-7.81 (m, 2H), 7.76-7.70 (m, 1H), 2.37-2.30 (m, 2H), 2.28-2.22 (m, 1H), 2.22-2.13 (m, 2H), 1.82-1.72 (m, 1H), 1.62-1.43 (m, 2H), 1.39-1.29 (m, 2H), 1.29-1.21 (m, 1H), 1.19-1.08 (m, 1H), 0.79-0.70 (m, 1H); MS (DCI+) M/Z 459 (M+NH4)+.

Sources & evidence

ORD record: ord-cf1d5497198542eea32e6edf693f0973
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08629143B2

Reaction notes

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