3-(tert-Butylaminosulphonyl)benzeneboronic acid → N-tert-Butyl-3-{2-[4-(1,1-dioxo-1 $1(6)-thiomorpholin-4-ylmethyl)-phenylamino]-pyrrolo[2,1-f][1,2,4]triazin-7-yl}-benzenesulfonamide

HRID 1262213Notes

Reaction equation

HRID 1262213 reaction equation
Br[C:2]1[N:10]2[C:5]([CH:6]=[N:7][C:8]([NH:11][C:12]3[CH:17]=[CH:16][C:15]([CH2:18][N:19]4[CH2:24][CH2:23][S:22](=[O:26])(=[O:25])[CH2:21][CH2:20]4)=[CH:14][CH:13]=3)=[N:9]2)=[CH:4][CH:3]=1.[C:27]([NH:31][S:32]([C:35]1[CH:36]=[C:37](B(O)O)[CH:38]=[CH:39][CH:40]=1)(=[O:34])=[O:33])([CH3:30])([CH3:29])[CH3:28]>>[C:27]([NH:31][S:32]([C:35]1[CH:36]=[CH:37][CH:38]=[C:39]([C:2]2[N:10]3[C:5]([CH:6]=[N:7][C:8]([NH:11][C:12]4[CH:13]=[CH:14][C:15]([CH2:18][N:19]5[CH2:24][CH2:23][S:22](=[O:26])(=[O:25])[CH2:21][CH2:20]5)=[CH:16][CH:17]=4)=[N:9]3)=[CH:4][CH:3]=2)[CH:40]=1)(=[O:34])=[O:33])([CH3:30])([CH3:28])[CH3:29]

Participants

3

Reactant 2

HCID 441195383-(tert-Butylaminosulphonyl)benzeneboronic acidHCID 67424859(7-Bromo-pyrrolo[2,1-f][1,2,4]triazin-2-yl)-[4-(1,1-dioxo-1 $1(6)-thiomorpholin-4-ylmethyl)-phenyl]-amine

Product 1

HCID 86661690N-tert-Butyl-3-{2-[4-(1,1-dioxo-1 $1(6)-thiomorpholin-4-ylmethyl)-phenylamino]-pyrrolo[2,1-f][1,2,4]triazin-7-yl}-benzenesulfonamide

Procedure

N-tert-Butyl-3-{2-[4-(1,1-dioxo-1 $1(6)-thiomorpholin-4-ylmethyl)-phenylamino]-pyrrolo[2,1-f][1,2,4]triazin-7-yl}-benzenesulfonamide was prepared from (7-Bromo-pyrrolo[2,1-f][1,2,4]triazin-2-yl)-[4-(1,1-dioxo-1$1(6)-thiomorpholin-4-ylmethyl)-phenyl]-amine and 3-t-Butylsulfamoylphenylboronic acid in an analogous manner to Example 1031b. Product isolated as a yellow foam (90 mg, 71%). LCMS (m/e) 569 (M+H); 1H-NMR (CDCl3, 400 MHz) δ 8.79 (s, 1H), 8.72 (s, 1H), 8.17 (d, 1H, J=7.9 Hz), 7.87 (d, 1H, J=7.9 Hz), 7.63-7.53 (m, 3H), 7.33 (d, 2H, J=8.3 Hz), 7.13 (s, 1H), 7.03 (d, 1H, J=4.8 Hz), 6.84 (d, 1H, J=4.8 Hz), 4.92 (s, 1H), 3.63 (s, 2H), 3.14-3.04 (m, 4H), 3.04-2.96 (m, 4H), 1.22 (s, 9H).

Sources & evidence

ORD record
ord-c78919a63c4a427b86482bb300a33809
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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