HCID 117728336, compound → HCID 178420002, compound

HRID 1772660Notes

Reaction equation

Br[C:2]1[N:7]2[CH:8]=[C:9]([CH2:11][O:12][C:13]3[CH:22]=[CH:21][C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[N:14]=3)[N:10]=[C:6]2[C:5]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)=[N:4][CH:3]=1.[NH:29]1[C:33]([C:34]2[CH:39]=[CH:38][C:37](B(O)O)=[CH:36][CH:35]=2)=[N:32][N:31]=[N:30]1>>[NH:32]1[C:33]([C:34]2[CH:39]=[CH:38][C:37]([C:2]3[N:7]4[CH:8]=[C:9]([CH2:11][O:12][C:13]5[CH:22]=[CH:21][C:20]6[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=6)[N:14]=5)[N:10]=[C:6]4[C:5]([N:23]4[CH2:28][CH2:27][O:26][CH2:25][CH2:24]4)=[N:4][CH:3]=3)=[CH:36][CH:35]=2)=[N:29][N:30]=[N:31]1

Participants

Reactant 2

HCID 117728336HCID 117728336, compound

HCID 178514828HCID 178514828, compound

Product 1

HCID 178420002HCID 178420002, compound

Procedure

Compound 31b was subjected to Suzuki coupling reaction conditions with (4-(1H-tetrazol-5-yl)phenyl)boronic acid using the methods described in Example 1, Step G to obtain compound 31c. 1H-NMR (400 MHz, DMSO-d6) 8.26 (d, J=8.6 Hz, 1H), 8.21 (d, J=8.6 Hz, 2H), 8.17 (s, 1H), 7.88-7.93 (m, 3H), 7.80 (d, J=8.6 Hz, 1H), 7.65-7.71 (m, 1H), 7.55 (s, 1H), 7.45 (t, J=7.0 Hz, 1H), 7.06 (d, J=9.0 Hz, 1H), 5.58 (s, 2H), 4.21-4.28 (m, 4H), 3.75-3.80 (m, 4H). Mass Spectrum (LCMS, ESI pos.) Calcd. for C27H23N9O2: 506.2 (M+H). Found 506.2.

Sources & evidence

ORD record: ord-4f6b6aec65d04c33b473c7ae257984d0
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09249163B2

Reaction notes

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