3-(tert-Butylaminosulphonyl)benzeneboronic acid → HCID 66710966, compound

HRID 1262082Notes

Reaction equation

HRID 1262082 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]([N:18]4[CH2:23][CH2:22][CH:21]([N:24]5[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]5)[CH2:20][CH2:19]4)=[CH:14][C:13]=3[O:31][CH3:32])=[N:9]2)=[CH:4][CH:3]=1.[C:33]([NH:37][S:38]([C:41]1[CH:42]=[C:43](B(O)O)[CH:44]=[CH:45][CH:46]=1)(=[O:40])=[O:39])([CH3:36])([CH3:35])[CH3:34]>>[C:33]([NH:37][S:38]([C:41]1[CH:42]=[CH:43][CH:44]=[C:45]([C:2]2[N:10]3[C:5]([CH:6]=[N:7][C:8]([NH:11][C:12]4[CH:17]=[CH:16][C:15]([N:18]5[CH2:23][CH2:22][CH:21]([N:24]6[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]6)[CH2:20][CH2:19]5)=[CH:14][C:13]=4[O:31][CH3:32])=[N:9]3)=[CH:4][CH:3]=2)[CH:46]=1)(=[O:40])=[O:39])([CH3:36])([CH3:34])[CH3:35]

Participants

3

Reactant 2

HCID 441195383-(tert-Butylaminosulphonyl)benzeneboronic acidHCID 66711255(7-Bromo-pyrrolo[2,1-f][1,2,4]triazin-2-yl)-{2-methoxy-4-[4-(4-methyl-piperazin-1-yl)-piperidin-1-yl]-phenyl}-amine

Product 1

HCID 66710966HCID 66710966, compoundYield 51%

Procedure

Following the procedure of example 532 (D), (7-Bromo-pyrrolo[2,1-f][1,2,4]triazin-2-yl)-{2-methoxy-4-[4-(4-methyl-piperazin-1-yl)-piperidin-1-yl]-phenyl}-amine (0.050 g, 0.00010 mol) and 3-t-Butylsulfamoylphenylboronic acid (0.028 g, 0.00011 mol) were reacted. Purification by prep plate chromatography gave N-tert-Butyl-3-(2-{2-methoxy-4-[4-(4-methyl-piperazin-1-yl)-piperidin-1-yl]-phenylamino}-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-benzenesulfonamide as a tan solid (0.032 g, 51%). MP: 214-216° C.; 1H-NMR (DMSO-d6, 400 MHz) δ 8.96 (s, 1H), 8.54 (s, 1H), 8.35-8.34 (d, 1H), 7.80 (t, 1H), 7.78-7.77 (d, 1H, J=2.88 Hz), 7.66 (t, 1H), 7.58 (s, 1H), 7.20-7.19 (d, 1H, J=4.80 Hz), 6.97-6.96 (d, 1H, J=4.72 Hz), 6.66 (s, 1H), 6.62-6.60 (d, 1H), 3.83 (s, 3H), 3.73-3.70 (d, 2H), 2.70-2.63 (m, 2H), 2.38-2.25 (m, 4H), 2.14 (s, 3H), 1.89-1.81 (d, 2H), 1.60-1.45 (q, 2H).

Workup

  1. customwere reacted
  2. customPurification by prep plate chromatography

Sources & evidence

ORD record
ord-22b0c73e229a4924886c2ed9739c042f
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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