5,6,7,8-Tetrahydro-1,6-naphthyridine--hydrogen chloride (1/1) → 3-[(4-(7,8-Dihydro-1,6-naphthyridin-6(5H)-yl)-1,3,5-triazin-2-yl)amino]-benzenemethanesulfonamide

HRID 587170Notes

Reaction equation

HRID 587170 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[CH:10]=[C:11]([CH2:15][S:16]([NH2:19])(=[O:18])=[O:17])[CH:12]=[CH:13][CH:14]=2)[N:3]=1.Cl.[N:21]1[C:30]2[CH2:29][CH2:28][NH:27][CH2:26][C:25]=2[CH:24]=[CH:23][CH:22]=1>>[N:21]1[C:30]2[CH2:29][CH2:28][N:27]([C:2]3[N:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]4[CH:10]=[C:11]([CH2:15][S:16]([NH2:19])(=[O:18])=[O:17])[CH:12]=[CH:13][CH:14]=4)[N:3]=3)[CH2:26][C:25]=2[CH:24]=[CH:23][CH:22]=1

Participants

3

Reactant 2

HCID 216997015,6,7,8-Tetrahydro-1,6-naphthyridine--hydrogen chloride (1/1)HCID 866798223-[(4-Chloro-1,3,5-triazin-2-yl)amino]benzenemethanesulfonamide

Product 1

HCID 601976013-[(4-(7,8-Dihydro-1,6-naphthyridin-6(5H)-yl)-1,3,5-triazin-2-yl)amino]-benzenemethanesulfonamide

Procedure

B38 was prepared following the general procedure reported for B10 using A1 and 5,6,7,8-tetrahydro-1,6-naphthyridine hydrochloride. The title compound (B38) was purified by reverse phase RP-HPLC (column: C18), using H2O (0.1% TFA) and MeOH (0.1% TFA) as eluents; yield: 67.6 mg (17%), colorless amorphous solid. 1H NMR (400 MHz, d6-DMSO, 300K) δ 2.98 (bs, 2H), 4.12 (t, J=6.0 Hz, 2H), 4.26 (bs, 2H), 4.95 (s, 2H), 6.86 (bs, 2H), 7.02 (d, J=7.9 Hz, 1H), 7.25 (dd, J=7.8 Hz, J=4.7 Hz, 1H), 7.31 (t, J=7.9 Hz, 1H), 7.47-7.80 (bm, 2H), 7.83-8.10 (bm, 1H), 8.39 (dd, J=4.8 Hz, J=1.6 Hz, 1H), 8.30 (s, 1H), 9.77 (s, 1H). MS (ES) C18H19N7O2S requires: 397. found: 398 (M+H)+.

Workup

  1. customB38 was prepared
  2. customThe title compound (B38) was purified by reverse phase RP-HPLC (column: C18)

Sources & evidence

ORD record
ord-a1a6a7b5da744a07b907ea6f7541b34f
Source dataset
uspto-grants-2016_01
Patent number
US09226929B2

Reaction notes

Loading…