rac-3-[(4-(2-Methoxymethylpiperidin-1-yl)-1,3,5-triazin-2-yl)amino]-benzenemethanesulfonamide → (R)-3-[(4-(2-(Benzyloxymethyl)pyrrolidin-1-yl)-1,3,5-triazin-2-yl)amino]benzenemethanesulfonamide

HRID 587163Notes

Reaction equation

HRID 587163 reaction equation
[CH3:1][O:2][CH2:3][CH:4]1CCCC[N:5]1[C:10]1[N:15]=[CH:14][N:13]=[C:12]([NH:16][C:17]2[CH:18]=[C:19]([CH2:23][S:24]([NH2:27])(=[O:26])=[O:25])[CH:20]=[CH:21][CH:22]=2)[N:11]=1.ClC1N=CN=C(N[C:36]2[CH:37]=[C:38](CS(N)(=O)=O)[CH:39]=[CH:40][CH:41]=2)N=1.ClC1N=CN=C(N[C:55]2[CH:56]=C(CCS(N)(=O)=O)C=C[CH:60]=2)N=1>>[CH2:1]([O:2][CH2:3][C@H:4]1[CH2:56][CH2:55][CH2:60][N:5]1[C:10]1[N:15]=[CH:14][N:13]=[C:12]([NH:16][C:17]2[CH:18]=[C:19]([CH2:23][S:24]([NH2:27])(=[O:25])=[O:26])[CH:20]=[CH:21][CH:22]=2)[N:11]=1)[C:41]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

Participants

4

Reactant 3

HCID 60197106rac-3-[(4-(2-Methoxymethylpiperidin-1-yl)-1,3,5-triazin-2-yl)amino]-benzenemethanesulfonamideHCID 866798223-[(4-Chloro-1,3,5-triazin-2-yl)amino]benzenemethanesulfonamideHCID 866798252-[3-((4-Chloro-1,3,5-triazin-2-yl)amino)phenyl]ethanesulfonamide

Product 1

HCID 60197502(R)-3-[(4-(2-(Benzyloxymethyl)pyrrolidin-1-yl)-1,3,5-triazin-2-yl)amino]benzenemethanesulfonamide

Procedure

B30 was prepared following the procedure reported for B4 using A1 and A4 and obtained as a white powder; yield: 270 mg (66%). 1H NMR (300 MHz, d6-DMSO, 300K) δ 1.82-2.08 (m, 4H), 3.42-3.78 (m, 4H), 4.20 (2 s, 2H), 4.24-4.39 (m, 1H), 4.39-4.58 (m, 2H), 6.85 (bs, 2H), 6.93-7.02 (m, 1H), 7.18-7.39 (m, 6H), 7.67-7.77 (m, 1H), 7.73 and 7.88 (2bs, 1H), 8.21 (2 s, 1H), 9.67 (s, 1H). MS (ES) C22H26N6O3S requires: 454. found: 455 (M+H)+.

Workup

  1. customB30 was prepared
  2. customobtained as a white powder

Sources & evidence

ORD record
ord-d844761efb344e09a4f007627a3588e0
Source dataset
uspto-grants-2016_01
Patent number
US09226929B2

Reaction notes

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