2-Phenylazetidine → rac-3-[(4-(2-Phenylazetidin-1-yl)-1,3,5-triazin-2-yl)amino]-benzenemethanesulfonamide

HRID 587169Notes

Reaction equation

HRID 587169 reaction equation
CO[CH2:3][CH:4]1[CH2:9][CH2:8][CH2:7][CH2:6][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(CS(N)(=O)=O)C=C[CH:41]=2)N=1.C1(C2CCN2)C=CC=CC=1>>[C:9]1([CH:4]2[CH2:3][CH2:6][N:5]2[C:10]2[N:15]=[CH:14][N:13]=[C:12]([NH:16][C:17]3[CH:18]=[C:19]([CH2:23][S:24]([NH2:27])(=[O:26])=[O:25])[CH:20]=[CH:21][CH:22]=3)[N:11]=2)[CH:37]=[CH:36][CH:41]=[CH:7][CH:8]=1

Participants

4

Reactant 3

HCID 5689712-PhenylazetidineHCID 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]benzenemethanesulfonamide

Product 1

HCID 60197600rac-3-[(4-(2-Phenylazetidin-1-yl)-1,3,5-triazin-2-yl)amino]-benzenemethanesulfonamide

Procedure

B37 was prepared following the general procedure reported for B4 using A1 and rac-2-phenylazetidine and obtained as white crystals; yield: 120 mg (34%). 1H NMR (300 MHz, d6-DMSO, 300K) δ 2.05-2.20 (m, 1H), 2.69-2.90 (m, 1H), 3.88-4.29 (m, 4H), 5.42 (bs, 1H), 6.72-7.08 (m, 3H), 7.20-7.55 (m, 6H), 7.58-7.72 and 7.82-8.00 (2 m, 1H), 8.11 and 8.25 (2bs, 1H), 9.65 and 9.78 (2bs, 1H). MS (ES) C19H20N6O2S requires: 396. found: 397 (M+H)+.

Workup

  1. customB37 was prepared
  2. customobtained as white crystals

Sources & evidence

ORD record
ord-f8952f2ce02a448083b1d0123efc9a41
Source dataset
uspto-grants-2016_01
Patent number
US09226929B2

Reaction notes

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