2-Bromopyrimidine → HCID 56599529, compound

HRID 514067Notes

Reaction equation

[C:1]([O:5][C@@H:6]([C:10]1[C:19]([CH3:20])=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[C:15]([C:21]3[N:26]=[CH:25][CH:24]=CN=3)[CH:16]=2)[C:11]=1[C:27]1[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=1)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:3])[CH3:2].Br[C:35]1N=CC=C[N:36]=1>>[C:1]([O:5][C@@H:6]([C:10]1[C:19]([CH3:20])=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[C:15]([C:21]3[CH:35]=[N:36][CH:24]=[CH:25][N:26]=3)[CH:16]=2)[C:11]=1[C:27]1[CH:28]=[CH:29][C:30]([Cl:33])=[CH:31][CH:32]=1)[C:7]([OH:9])=[O:8])([CH3:2])([CH3:3])[CH3:4]

Participants

Reactant 2

HCID 783452-Bromopyrimidine

HCID 67126276HCID 67126276, compound

Product 1

HCID 56599529HCID 56599529, compound

Procedure

(S)-2-tert-butoxy-2-(1-(4-chlorophenyl)-3-methyl-6-(pyrazin-2-yl)naphthalen-2-yl)acetic acid was prepared in a similar fashion to compound 59 with the substitution of 2-chloropyrazine for 2-bromopyrimidine in step 2. The title compound (0.026 g) was isolated as an amorphous pale yellow powder. LCMS-ESI+ (m/z): [M+H]+ calcd for C27H26ClN2O3: 461.96; found: 461.30. 1H-NMR: 400 MHz, (CD3CN) δ: 9.23 (s, 1H); 8.67 (s, 1H); 8.56 (s, 2H); 8.05 (d, J=8.8 Hz, 1H); 7.89 (s, 1H); 7.61-7.54 (m, 3H); 7.42 (d, J=8.8 Hz, 1H); 7.39 (br d, J=8.8 Hz, 1H); 5.23 (s, 1H); 2.60 (s, 3H); 1.00 (s, 9H).

Sources & evidence

ORD record: ord-a50e6fae70c14cefba5db8302b0ed675
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09102614B2

Reaction notes

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