1-(Methylsulfonyl)-1,2,3,4-tetrahydroquinolin-7-amine → N-tert-Butyl-3-[2-(1-methanesulfonyl-1,2,3,4-tetrahydro-quinolin-7-ylamino)-pyrrolo[2,1-f][1,2,4]triazin-7-yl]-benzenesulfonamide

HRID 1262217Notes

Reaction equation

HRID 1262217 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].[CH3:25][S:26]([N:29]1[C:38]2[C:33](=[CH:34][CH:35]=[C:36]([NH2:39])[CH:37]=2)[CH2:32][CH2:31][CH2:30]1)(=[O:28])=[O:27]>>[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:39][C:36]4[CH:37]=[C:38]5[C:33]([CH2:32][CH2:31][CH2:30][N:29]5[S:26]([CH3:25])(=[O:28])=[O:27])=[CH:34][CH:35]=4)=[N:22]3)=[CH:17][CH:16]=2)[CH:10]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 91252911-(Methylsulfonyl)-1,2,3,4-tetrahydroquinolin-7-amineHCID 178449976HCID 178449976, compound

Product 1

HCID 46851710N-tert-Butyl-3-[2-(1-methanesulfonyl-1,2,3,4-tetrahydro-quinolin-7-ylamino)-pyrrolo[2,1-f][1,2,4]triazin-7-yl]-benzenesulfonamide

Procedure

N-tert-Butyl-3-[2-(1-methanesulfonyl-1,2,3,4-tetrahydro-quinolin-7-ylamino)-pyrrolo[2,1-f][1,2,4]triazin-7-yl]-benzenesulfonamide was prepared from N-tert-butyl-3-(2-hydroxy-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-benzenesulfonamide and 1-methanesulfonyl-1,2,3,4-tetrahydro-quinolin-7-ylamine in an analogous manner to Example 1052a. Product isolated as a yellow solid (69 mg, 57%). m.p.=187-191° C.; LCMS (m/e) 555 (M+H); 1H-NMR (d6-DMSO, 400 MHz) δ 9.50 (s, 1H), 9.04 (s, 1H), 8.51-8.42 (m, 2H), 7.82 (d, 1H, J=7.9 Hz), 7.76-7.65 (m, 3H), 7.62 (s, 1H), 7.20 (d, 1H, J=4.8 Hz), 7.16 (d, 1H, J=8.3 Hz), 6.99 (d, 1H, J=4.8 Hz), 3.73-3.67 (m, 2H), 3.00 (s, 3H), 2.78-2.71 (m, 2H), 1.97-1.87 (m, 2H), 1.11 (s, 9H).

Sources & evidence

ORD record
ord-edc14252e96a4711b24da93bb33d098e
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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