Dimethylamine → HCID 57942145, compound

HRID 1898167Notes

Reaction equation

HRID 1898167 reaction equation
[Cl:1][C:2]1[C:10]([C:11]([C:13]2[C:18]([NH:19][S:20]([C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[C:25]([C:30]([F:33])([F:32])[F:31])[CH:24]=3)(=[O:22])=[O:21])=[CH:17][C:16]([Cl:34])=[CH:15][N:14]=2)=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[CH3:35][N:36](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)[CH3:37].F[P-](F)(F)(F)(F)F.N(C)C.C1COCC1.CCN(C(C)C)C(C)C>CCOC(C)=O.CN(C=O)C>[Cl:1][C:2]1[C:10]([C:11]([C:13]2[C:18]([NH:19][S:20]([C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[C:25]([C:30]([F:33])([F:32])[F:31])[CH:24]=3)(=[O:22])=[O:21])=[CH:17][C:16]([Cl:34])=[CH:15][N:14]=2)=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([N:36]([CH3:37])[CH3:35])=[O:6]

Participants

8

Reactant 5

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57942362HCID 57942362, compound

Product 1

HCID 57942145HCID 57942145, compoundYield 22%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a vial containing 2-chloro-3-[5-chloro-3-(4-chloro-3-trifluoromethylbenzenesulfonyl amino)-pyridine-2-carbonyl]benzoic acid (24 mg, 0.04 mmol) were added HATU (19 mg, 0.05 mmol), DMF (0.5 mL), a 2.0 M solution of Me2NH in THF (40 μL, 0.08 mmol), and (i-Pr)2NEt (10 μL, 0.06 mmol). The solution was maintained at room temperature for 5 h. EtOAc (10 mL) was added, and the organic phase washed with saturated aqueous NaCl (1×5 mL), 0.1 N acetic acid in water (1×5 mL), and dried over MgSO4. The volatiles were removed in vacuo, and the resulting residue was purified by preparative HPLC (20→95% gradient of MeCN—H2O with 0.1% TFA) and the pure fractions lyophilized to afford the title compound (5 mg, 22% yield): HPLC retention time=2.90 minutes. MS (ES) [M+H]+ expected 580.0. found 579.9. 1H NMR (400 MHz, CDCl3) δ 10.94 (s, 1H), 8.17-8.20 (m, 3H), 7.98 (dd, J=2.4, 8.4 Hz, 1H), 7.64 (d, J=8.8 Hz, 1H), 7.41 (d, J=4.4 Hz, 1H), 7.28-7.30 (m, 2H), 3.12 (s, 3H), 2.86 (s, 3H).

Workup

  1. washthe organic phase washed with saturated aqueous NaCl (1×5 mL), 0.1 N acetic acid in water (1×5 mL)
  2. dry with materialdried over MgSO4
  3. customThe volatiles were removed in vacuo
  4. customthe resulting residue was purified by preparative HPLC (20→95% gradient of MeCN—H2O with 0.1% TFA)

Sources & evidence

ORD record
ord-76427381d35c459fb3364579d429549d
Source dataset
uspto-grants-2013_08
Patent number
US08519135B2

Reaction notes

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