Triethylamine → HCID 11271384, compound

HRID 1036759Notes

Reaction equation

HRID 1036759 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][S:36](Cl)(=[O:38])=[O:37]>CN(C=O)C>[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][N:25]([S:36]([CH3:35])(=[O:38])=[O:37])[CH2:24][CH2:23]3)[N:15]=[CH:14][N:13]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 11257886(4-Methanesulfonyl-phenyl)-[5-nitro-6-(piperidin-4-yloxy)-pyrimidin-4-yl]-amine2×

Product 1

HCID 11271384HCID 11271384, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Compound A27 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 (50 μl), methanesulfonyl chloride (10 mg, 0.087 mmol), DMF (1 mL), 1H NMR (CDCl3, 400 MHz) δ 2.13 (m,4H), 2.85 (s, 3H), 3.08 (s, 3H), 3.31 (m, 2H), 3.57 (m, 2H), 4.13 (m, 1H), 5.69 (m, 1H), 7.87 (d,2H), 7.98 (d,2H), 8.42 (s, 1H), 10.21 (s, 1H). Exact mass calculated for C14H21N5O7S2 471.09, found 472.3 (MH+).

Workup

  1. customCompound A27 was prepared in a similar manner

Sources & evidence

ORD record
ord-69282ffc79ce42c58446062a16deab69
Source dataset
uspto-grants-2013_10
Patent number
US08546429B2

Reaction notes

Loading…