2-Bromopyrimidine → HCID 56599530, compound

HRID 514068Notes

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]3N=CC=[CH:23][N:22]=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]1[N:40]=[CH:39][CH:38]=[CH:37][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[C:35]4[N:36]([CH:38]=[CH:39][N:40]=4)[CH:37]=[CH:23][N:22]=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])([CH3:3])([CH3:4])[CH3:2]

Participants

Reactant 2

HCID 783452-Bromopyrimidine

HCID 67126276HCID 67126276, compound

Product 1

HCID 56599530HCID 56599530, compound

Procedure

(S)-2-tert-butoxy-2-(1-(4-chlorophenyl)-6-(imidazo[1,2-a]pyrazin-8-yl)-3-methylnaphthalen-2-yl)acetic acid (61) was prepared in a similar fashion to compound 59 with the substitution of 8-chloroimidazo[1,2-a]pyrazine hydrobromide (See Guzi, T. J, Paruch, K., et. al. US 20070105864, p. 121) for 2-bromopyrimidine in step 2. The title compound (0.017 g) was isolated as an amorphous pale yellow powder. LCMS-ESI+ (m/z): [M+H]+ calcd for C29H27ClN3O3: 500.7; found: 500.0. 1H-NMR: 400 MHz, (CD3CN) δ: 9.00 (d, J=1.2 Hz, 1H); 8.39 (d, J=4.4 Hz, 1H); 8.20 (dd, J=8.8, 1.2 Hz, 1H); 8.11 (d, J=4.4 Hz, 1H); 8.06 (d, J=1.2 Hz, 1H); 7.99 (s, 1H); 7.62-7.56 (m, 3H); 7.38 (d, J=8.8 Hz, 1H); 7.36 (br d, J=8.8 Hz, 1H); 5.25 (s, 1H); 2.58 (s, 3H); 0.99 (s, 9H).

Sources & evidence

ORD record: ord-5f7c10d7ae3d4772a1a2d326262c768c
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09102614B2

Reaction notes

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