HCID 178419312, compound → HCID 178508366, compound

HRID 389603Notes

Reaction equation

HRID 389603 reaction equation
[Si]([O:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([N:15]2[CH:19]=[C:18]([C:20]3[CH:25]=[N:24][C:23]([N:26](C(OC(C)(C)C)=O)C(OC(C)(C)C)=O)=[C:22]4[O:41][C:42]([Sn](C)(C)C)=[CH:43][C:21]=34)[CH:17]=[N:16]2)[CH2:11][CH2:10]1)(C(C)(C)C)(C)C.Br[C:49]1[C:57]2[S:56][N:55]=[N:54][C:53]=2[CH:52]=[C:51]([C:58]2[CH:62]=[CH:61][NH:60][N:59]=2)[CH:50]=1>>[NH2:26][C:23]1[N:24]=[CH:25][C:20]([C:18]2[CH:17]=[N:16][N:15]([C@H:12]3[CH2:13][CH2:14][C@H:9]([OH:8])[CH2:10][CH2:11]3)[CH:19]=2)=[C:21]2[CH:43]=[C:42]([C:49]3[C:57]4[S:56][N:55]=[N:54][C:53]=4[CH:52]=[C:51]([C:58]4[CH:62]=[CH:61][NH:60][N:59]=4)[CH:50]=3)[O:41][C:22]=12

Participants

3

Reactant 2

HCID 178419312HCID 178419312, compoundHCID 178454345HCID 178454345, compound

Product 1

HCID 178508366HCID 178508366, compound

Procedure

The title compound was prepared from di-tert-butyl {4-[1-(trans-4-{[tert-butyl(dimethyl)silyl]oxy}cyclohexyl)-1H-pyrazol-4-yl]-2-(trimethylstannanyl)furo[2,3-c]pyridin-7-yl}imidodicarbonate and 7-bromo-5-(1H-pyrazol-3-yl)-1,2,3-benzothiadiazole by a procedure analogous to Example 373, Step B. 1H NMR (400 MHz, CD3OD): δ 1.50-1.61 (m, 2 H), 1.93-2.06 (m, 2 H), 2.13-2.21 (m, 2 H), 2.25-2.33 (m, 2 H), 3.75 (tdd, J=10.9, 10.9, 4.2, 4.0 Hz, 1 H), 4.27 (tdd, J=12.0, 12.0, 4.3, 4.1 Hz, 1 H), 6.97 (d, J=2.3 Hz, 1 H), 7.58 (s, 1 H), 7.78 (d, J=2.3 Hz, 1 H), 7.88 (s, 1 H), 7.93 (s, 1 H), 7.94 (s, 1 H), 8.92 (br. s, 1 H), 9.04 (d, J=1.3 Hz, 1 H).

Sources & evidence

ORD record
ord-ca32b580da3f4bb1b52b462a9321b3ca
Source dataset
uspto-grants-2013_02
Patent number
US08378104B2

Reaction notes

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