Triethylamine → HCID 11386720, compound

HRID 2377887Notes

Reaction equation

HRID 2377887 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.[CH2:35]([S:39](Cl)(=[O:41])=[O:40])[CH2:36][CH2:37][CH3:38]>CN(C=O)C>[CH2:35]([S:39]([N:25]1[CH2:26][CH2:27][CH:22]([O:21][C:16]2[N:15]=[CH:14][N:13]=[C:12]([NH:11][C:8]3[CH:9]=[CH:10][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:6][CH:7]=3)[C:17]=2[N+:18]([O-:20])=[O:19])[CH2:23][CH2:24]1)(=[O:41])=[O:40])[CH2:36][CH2:37][CH3:38]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 754301-Butanesulfonyl chlorideHCID 11257886(4-Methanesulfonyl-phenyl)-[5-nitro-6-(piperidin-4-yloxy)-pyrimidin-4-yl]-amine

Product 1

HCID 11386720HCID 11386720, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Compound A29 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., Comound A2) (15 mg, 0.035 mmol), triethylamine (20 μl), butane-1-sulfonyl chloride (8 mg, 0.056 mmol), DMF (0.6 mL), 1H NMR (CDCl3, 400 MHz) δ 0.98 (t,3H), 1.51 (m,2H), 1.83 (m,2H), 2.07 (m,4H), 2.97 (m, 2H), 3.08 (s, 3H), 3.40 (m, 2H), 3.58 (m, 2H), 5.68 (m, 1H), 7.87 (d, 2H), 7.98 (d, 2H), 8.41 (s, 1H), 10.21 (s, 1H). Exact mass calculated for C20H27N5O7S2 513.14, found 514.4 (MH+).

Workup

  1. customCompound A29 was prepared in a similar manner

Sources & evidence

ORD record
ord-c14844a9ce864ee285fac1289b9241ec
Source dataset
uspto-grants-2008_12
Patent number
US07470699B2

Reaction notes

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