4-((2-Bromophenyl)sulfonyl)thiomorpholine 1,1-dioxide → 4-((4'-(5-Amino-1,3,4-thiadiazol-2-yl)-3'-fluoro-[1,1'-biphenyl]-2-yl)sulfonyl)thiomorpholine 1,1-dioxide

HRID 1523950Notes

Reaction equation

HRID 1523950 reaction equation
[F:1][C:2]1[CH:7]=[C:6](B2OC(C)(C)C(C)(C)O2)[CH:5]=[CH:4][C:3]=1[C:17]1[S:21][C:20]([NH2:22])=[N:19][N:18]=1.Br[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[S:30]([N:33]1[CH2:38][CH2:37][S:36](=[O:40])(=[O:39])[CH2:35][CH2:34]1)(=[O:32])=[O:31]>>[NH2:22][C:20]1[S:21][C:17]([C:3]2[CH:4]=[CH:5][C:6]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[S:30]([N:33]3[CH2:34][CH2:35][S:36](=[O:39])(=[O:40])[CH2:37][CH2:38]3)(=[O:31])=[O:32])=[CH:7][C:2]=2[F:1])=[N:18][N:19]=1

Participants

3

Reactant 2

HCID 549220134-((2-Bromophenyl)sulfonyl)thiomorpholine 1,1-dioxideHCID 903143255-(2-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,4-thiadiazol-2-amine

Product 1

HCID 903136094-((4'-(5-Amino-1,3,4-thiadiazol-2-yl)-3'-fluoro-[1,1'-biphenyl]-2-yl)sulfonyl)thiomorpholine 1,1-dioxide

Procedure

The title compound was prepared using analogous conditions to those described in Example 6 utilizing 5-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,4-thiadiazol-2-amine and 4-((2-bromophenyl)sulfonyl)thiomorpholine 1,1-dioxide. MS (ESI): mass calcd. for C18H17FN4O4S2, 468.04; m/z found, 469.0 [M+H]+. 1H NMR (300 MHz, CD3OD) δ 8.19 (m, 1H), 8.15 (dd, J=8.0, 1.1, 1H), 7.76 (m, 1H), 7.67 (m, 1H), 7.45 (dd, J=7.6, 1.2, 1H), 7.39 (dd, J=11.9, 1.4, 1H), 7.36 (dd, J=8.1, 1.6, 1H), 3.42-3.33 (m, 4H), 3.09-3.02 (m, 4H).

Sources & evidence

ORD record
ord-01a165443e014b0faa2c8fec22421e57
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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