HCID 86700215, compound → HCID 86700401, compound

HRID 879585Notes

Reaction equation

[C:1]([O:5][C@@H:6]([C:12]1[C:30]([CH3:31])=[CH:29][C:15]2[N:16]=[C:17](C3C=CC4N(C)N=NC=4C=3)[S:18][C:14]=2[C:13]=1[C:32]1[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:4])([CH3:3])[CH3:2].[CH3:39][C:40]1[N:41]=[C:42]([CH3:58])[N:43]2[CH:48]=[CH:47][C:46](B3OC(C)(C)C(C)(C)O3)=[CH:45][C:44]=12>>[C:1]([O:5][C@@H:6]([C:12]1[C:30]([CH3:31])=[CH:29][C:15]2[N:16]=[C:17]([C:46]3[CH:47]=[CH:48][N:43]4[C:42]([CH3:58])=[N:41][C:40]([CH3:39])=[C:44]4[CH:45]=3)[S:18][C:14]=2[C:13]=1[C:32]1[CH:33]=[CH:34][C:35]([Cl:38])=[CH:36][CH:37]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:2])([CH3:3])[CH3:4]

Participants

Reactant 2

HCID 86700215HCID 86700215, compound

HCID 86700402HCID 86700402, compound

Product 1

HCID 86700401HCID 86700401, compound

Procedure

Prepared in manner similar to (S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(1-methyl-1H-benzo[d][1,2,3]triazol-5-yl)benzo[d]thiazol-6-yl)acetate, but using 1,3-dimethyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)imidazo[1,5-a]pyridine instead of 1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzo[d][1,2,3]triazole. 1H NMR (400 MHz, CDCl3) δ 7.94 (s, 1H), 7.82 (s, 1H), 7.61 (d, J=7.6 Hz, 1H), 7.51 (dt, J=14.3, 7.8 Hz, 5H), 5.15 (s, 1H), 4.21 (dd, J=5.9, 3.5 Hz, 2H), 2.67 (s, 3H), 2.59 (s, 3H), 2.54 (s, 3H), 1.25 (t, J=6.0 Hz, 3H), 0.98 (s, 9H).

Sources & evidence

ORD record: ord-ab1ef74a58154a0e849ae38f9aba65ae
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987250B2

Reaction notes

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