HCID 69905525, compound → HCID 71765432, compound

HRID 2203222Notes

Reaction equation

[CH:1]1([N:7]2[C:11]3[CH:12]=[CH:13][C:14](B4OC(C)(C)C(C)(C)O4)=[CH:15][C:10]=3[N:9]=[CH:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:25][C:26]1[C:35]2[C:30](=[C:31](Br)[CH:32]=[CH:33][CH:34]=2)[N:29]=[N:28][C:27]=1[C:37]([NH2:39])=[O:38]>>[NH2:25][C:26]1[C:35]2[C:30](=[C:31]([C:14]3[CH:13]=[CH:12][C:11]4[N:7]([CH:1]5[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]5)[CH:8]=[N:9][C:10]=4[CH:15]=3)[CH:32]=[CH:33][CH:34]=2)[N:29]=[N:28][C:27]=1[C:37]([NH2:39])=[O:38]

Participants

Reactant 2

HCID 69905525HCID 69905525, compound

HCID 71119070HCID 71119070, compound

Product 1

HCID 71765432HCID 71765432, compound

Procedure

The title compound was prepared in a manner similar to EXAMPLE 1 using 1-cyclohexyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzo[d]imidazole and 4-amino-8-bromocinnoline-3-carboxamide. 1H NMR (400 MHz, CD3OD) δ ppm 1.29 (t, J=8 Hz, 1 H), 1.44 (br s, 1 H), 1.52-1.71 (m, 2 H), 1.83 (d, J=12 Hz, 1 H), 1.88-2.08 (m, 3 H), 2.13-2.30 (m, 2 H), 7.58 (d, J=8 Hz, 1 H), 7.66-7.83 (m, 2 H), 7.83-7.96 (m, 2 H), 8.28 (d, J=8 Hz, 1 H), 8.35 (br s, 1 H), 8.62 (s, 1 H); ESI-MS m/z [M+H]+ 387.4.

Sources & evidence

ORD record: ord-343913349f724afebbb510830e5cfaf0
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09365566B2

Reaction notes

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