Triethylamine → HCID 11180141, compound

HRID 1174735Notes

Reaction equation

HRID 1174735 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.[Cl:35][C:36]1[N:44]=[CH:43][CH:42]=[CH:41][C:37]=1[C:38](Cl)=[O:39]>CN(C=O)C>[Cl:35][C:36]1[C:37]([C:38]([N:25]2[CH2:26][CH2:27][CH:22]([O:21][C:16]3[C:17]([N+:18]([O-:20])=[O:19])=[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)[N:13]=[CH:14][N:15]=3)[CH2:23][CH2:24]2)=[O:39])=[CH:41][CH:42]=[CH:43][N:44]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27745412-Chloronicotinoyl chlorideHCID 11257886(4-Methanesulfonyl-phenyl)-[5-nitro-6-(piperidin-4-yloxy)-pyrimidin-4-yl]-amine2×

Product 1

HCID 11180141HCID 11180141, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Compound A25 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) (16 mg, 0.037 mmol), triethylamine (50 μl), 2-chloro-nicotinoyl chloride (10 mg, 0.046 mmol), DMF (1 mL), 1H NMR (CDCl3, 400 MHz) δ 1.91 (m, 1H), 2.00 (m, 1H), 2.14 (m, 2H), 3.08 (s, 3H), 3.36 (m, 1H), 3.65 (m, 2H), 4.13 (m, 1H), 4.31 (m, 1H), 5.72 (m, 1H), 7.36 (m, 1H), 7.69 (m, 1H), 7.87 (d, 2H), 7.97 (d, 2H), 8.41 (m, 1H), 8.47 (m, 1H), 10.20 (s, 1H). Exact mass calculated for C22H21ClN6O6S 532.09, found 533.3 (MH+).

Workup

  1. customCompound A25 was prepared in a similar manner

Sources & evidence

ORD record
ord-0dec1494acf74ffbb3eb9852c5eed098
Source dataset
uspto-grants-2010_11
Patent number
US07838525B2

Reaction notes

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