Phenyl triflimide → HCID 66711278, compound

HRID 1262107Notes

Reaction equation

[C:1]([NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]2[N:23]3[C:18]([CH:19]=[N:20][C:21](O)=[N:22]3)=[CH:17][CH:16]=2)[CH:10]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:25][C:26]1[CH:31]=[CH:30][C:29]([CH:32]2[CH2:37][CH2:36][N:35]([CH2:38][CH2:39][OH:40])[CH2:34][CH2:33]2)=[CH:28][CH:27]=1.C1C=CC(N(S(C(F)(F)F)(=O)=O)S(C(F)(F)F)(=O)=O)=CC=1>>[C:1]([NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]2[N:23]3[C:18]([CH:19]=[N:20][C:21]([NH:25][C:26]4[CH:31]=[CH:30][C:29]([CH:32]5[CH2:37][CH2:36][N:35]([CH2:38][CH2:39][OH:40])[CH2:34][CH2:33]5)=[CH:28][CH:27]=4)=[N:22]3)=[CH:17][CH:16]=2)[CH:10]=1)(=[O:8])=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

Reactant 3

HCID 142176Phenyl triflimide

HCID 574160902-[4-(4-Aminophenyl)piperidin-1-yl]ethan-1-ol

HCID 178449976HCID 178449976, compound

Product 1

HCID 66711278HCID 66711278, compound

Procedure

The titled compound was prepared in analogous fashion as Example 522 using N-tert-butyl-3-(2-hydroxy-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-benzenesulfonamide, 2-[4-(4-amino-phenyl)-piperidin-1-yl]-ethanol and N-phenylbis(trifluoromethanesulphonimide) to give N-tert-butyl-3-(2-{4-[1-(2-hydroxy-ethyl)-piperidin-4-yl]-phenylamino}-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-benzenesulfonamide as a orange lyophilate (150.9 mg, 82% yield). LCMS (E/I+) 549 (M+H). 1H NMR (400 MHz, DMSO-d6) δ 9.53 (s, 1H), 9.27 (s, 1H), 9.04 (s, 1H), 8.58 (s, 1H), 8.33 (d, 1H, J=7.8 Hz), 7.87 (d, 1H, J=7.8 Hz), 7.72 (d, 2H, J=7.6 Hz), 7.60 (s, 1H), 7.21 (m, 3H), 7.0 (d, 1H, J=4.5 Hz), 3.78 (t, 2H, J=5 Hz), 3.61 (d, 2H, J=11 Hz), 3.38 (m, 1H), 3.18 (m, 2H), 3.12 (m, 2H), 2.76 (m, 1H), 1.97 (m, 4H), 1.11 (s, 9H).

Sources & evidence

ORD record: ord-a7158def71c6441abae0bc4f9af3ce7a
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08471005B2

Reaction notes

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