Triethylamine → {6-[1-(2,4-Dimethyl-thiazole-5-sulfonyl)piperidin-4-yloxy]-5-nitro-pyrimidin-4-yl}-(4-methanesulfonyl-phenyl)-amine

HRID 1036764Notes

Reaction equation

HRID 1036764 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[C:17]([N+:18]([O-:20])=[O:19])=[C:16]([O:21][CH:22]3[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]3)[N:15]=[CH:14][N:13]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].C(N(CC)CC)C.[CH3:35][C:36]1[S:37][C:38]([S:42](Cl)(=[O:44])=[O:43])=[C:39]([CH3:41])[N:40]=1>CN(C=O)C>[CH3:35][C:36]1[S:37][C:38]([S:42]([N:25]2[CH2:26][CH2:27][CH:22]([O:21][C:16]3[N:15]=[CH:14][N:13]=[C:12]([NH:11][C:8]4[CH:9]=[CH:10][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:6][CH:7]=4)[C:17]=3[N+:18]([O-:20])=[O:19])[CH2:23][CH2:24]2)(=[O:44])=[O:43])=[C:39]([CH3:41])[N:40]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2776248Dimethyl-1,3-thiazole-5-sulfonyl chlorideHCID 11257886(4-Methanesulfonyl-phenyl)-[5-nitro-6-(piperidin-4-yloxy)-pyrimidin-4-yl]-amine2×

Product 1

HCID 59856716{6-[1-(2,4-Dimethyl-thiazole-5-sulfonyl)piperidin-4-yloxy]-5-nitro-pyrimidin-4-yl}-(4-methanesulfonyl-phenyl)-amine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Compound A32 was prepared in a similar manner as described above using (4-methanesulfonyl-phenyl)-[5-nitro-6-(piperidin-4-yloxy)-pyrimidin-4-yl]-amine (i.e., Compound A2) (15 mg, 0.035 mmol), triethylamine (20 μl), 2,4-dimethyl-thiazole-5-sulfonyl chloride (10 mg, 0.047 mmol), DMF (0.6 mL), 1H NMR (CDCl3, 400 MHz) δ 2.09 (m, 4H), 2.67 (s, 3H), 2.75 (s,3H), 3.08 (s, 3H), 3.21 (m, 2H), 3.50 (m, 2H), 5.58 (m, 1H), 7.85 (d,2H), 7.97 (d, 2H), 8.38 (s, 1H), 10.14 (s, 1H). Exact mass calculated for C21H24N6O7S3 568.09, found 569.4 (MH+).

Workup

  1. customCompound A32 was prepared in a similar manner

Sources & evidence

ORD record
ord-a1532e7a5b5547de93215989d5ae3641
Source dataset
uspto-grants-2013_10
Patent number
US08546429B2

Reaction notes

Loading…