(2R)-2-(Methoxymethyl)pyrrolidine → (R)-3-[(4-(2-(Methoxymethyl)pyrrolidin-1-yl)-1,3,5-triazin-2-yl)amino]benzenemethanesulfonamide

HRID 587152Notes

Reaction equation

HRID 587152 reaction equation
[N:1]1([C:7]2[N:12]=[CH:11][N:10]=[C:9]([NH:13][C:14]3[CH:15]=[C:16]([CH2:20][S:21]([NH2:24])(=[O:23])=[O:22])[CH:17]=[CH:18][CH:19]=3)[N:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.ClC1N=CN=C(NC2C=C(CS(N)(=O)=O)C=CC=2)N=1.[CH3:44][O:45]C[C@H]1CCCN1>>[CH3:44][O:45][CH2:6][C@H:5]1[CH2:4][CH2:3][CH2:2][N:1]1[C:7]1[N:12]=[CH:11][N:10]=[C:9]([NH:13][C:14]2[CH:15]=[C:16]([CH2:20][S:21]([NH2:24])(=[O:23])=[O:22])[CH:17]=[CH:18][CH:19]=2)[N:8]=1

Participants

4

Reactant 3

HCID 671216(2R)-2-(Methoxymethyl)pyrrolidineHCID 601971013-[(4-(Piperidin-1-yl)-1,3,5-triazin-2-yl)amino]benzenemethane sulfonamideHCID 866798223-[(4-Chloro-1,3,5-triazin-2-yl)amino]benzenemethanesulfonamide

Product 1

HCID 60197304(R)-3-[(4-(2-(Methoxymethyl)pyrrolidin-1-yl)-1,3,5-triazin-2-yl)amino]benzenemethanesulfonamide

Procedure

B17 was prepared following the procedure reported for B1 using A1 and (R)-2-(methoxymethyl)pyrrolidine. 1H NMR (400 MHz, DMSO, 300K) δ 1.85-2.01 (m, 4H), 3.25 (s, 3H), 3.31-3.63 (m, 4H), 4.18-4.29 (m, 3H), 6.81 (s, 2H), 6.98 (t, J=8.4 Hz, 1H), 7.25 (dt, J=4.7 Hz, J=7.8 Hz, 1H), 7.65-7.87 (m, 2H), 8.20 (s, 1H), 9.63 (s, 1H). MS (ES) C16H22N6O3S requires: 378. found: 379 (M+H)+.

Workup

  1. customB17 was prepared

Sources & evidence

ORD record
ord-657b3cd4774b459783d76b56bd203389
Source dataset
uspto-grants-2016_01
Patent number
US09226929B2

Reaction notes

Loading…