1-((2-Bromophenyl)sulfonyl)piperidin-4-amine → 1-{[4'-(3,4-Dihydro-2H-pyrido[3,2-b][1,4]oxazin-7-yl)-3'-fluorobiphenyl-2-yl]sulfonyl}piperidin-4-amine

HRID 1523916Notes

Reaction equation

HRID 1523916 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH:8]2OC(C)(C)C(C)(C)O2)[CH:5]=[CH:4][C:3]=1[C:17]1[CH:26]=[N:25][C:24]2[NH:23][CH2:22][CH2:21][O:20][C:19]=2[CH:18]=1.Br[C:28]1[CH:33]=[CH:32][CH:31]=C[C:29]=1[S:34]([N:37]1[CH2:42][CH2:41][CH:40]([NH2:43])[CH2:39][CH2:38]1)(=[O:36])=[O:35]>>[O:20]1[CH2:21][CH2:22][NH:23][C:24]2[N:25]=[CH:26][C:17]([C:3]3[CH:4]=[CH:5][C:6]([C:8]4[CH:31]=[CH:32][CH:33]=[CH:28][C:29]=4[S:34]([N:37]4[CH2:42][CH2:41][CH:40]([NH2:43])[CH2:39][CH2:38]4)(=[O:36])=[O:35])=[CH:7][C:2]=3[F:1])=[CH:18][C:19]1=2

Participants

3

Reactant 2

HCID 289734911-((2-Bromophenyl)sulfonyl)piperidin-4-amineHCID 903140397-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3-dioxolan-2-yl)phenyl)-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine

Product 1

HCID 903137431-{[4'-(3,4-Dihydro-2H-pyrido[3,2-b][1,4]oxazin-7-yl)-3'-fluorobiphenyl-2-yl]sulfonyl}piperidin-4-amine

Procedure

The title compound was prepared in a manner similar to that described in Example 444 using 7-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3-dioxolan-2-yl)phenyl)-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine and 1-((2-bromophenyl)sulfonyl)piperidin-4-amine. MS (ESI): mass calcd. for C24H25FN4O3S, 468.16; m/z found, 469.1 [M+H]+. 1H NMR (400 MHz, CD3OD) δ 8.09-8.05 (m, 1H), 7.83 (d, J=1.1, 1H), 7.75-7.68 (m, 2H), 7.66-7.55 (m, 2H), 7.43-7.39 (m, 1H), 7.34-7.26 (m, 2H), 4.39-4.35 (m, 2H), 3.76-3.68 (m, 2H), 3.47 (d, J=13.4, 2H), 3.21-3.11 (m, 1H), 2.60-2.50 (m, 2H), 1.96-1.87 (m, 2H), 1.56-1.43 (m, 2H).

Sources & evidence

ORD record
ord-f0f5a2fd6d174dd29a07612009d2c548
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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