Diisopropylethylamine → N-methyl-N-2-[methyl(pyridin-2-yl)-amino]ethyl-4-[3-(1-quinolin-6-ylcyclopropyl)[1,2,4]triazolo[4,3-b][1,2,4]triazin-6-yl]benzamide

HRID 607615Notes

Reaction equation

HRID 607615 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]3([C:14]4[N:18]5[N:19]=[C:20]([C:23]6[CH:31]=[CH:30][C:26]([C:27]([OH:29])=O)=[CH:25][CH:24]=6)[CH:21]=[N:22][C:17]5=[N:16][N:15]=4)[CH2:13][CH2:12]3)=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.F[C:33](F)(F)C(O)=O.[CH3:39][N:40]([C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][N:45]=1)[CH2:41][CH2:42][NH2:43].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>C(Cl)Cl>[CH3:33][N:43]([CH2:42][CH2:41][N:40]([CH3:39])[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][N:45]=1)[C:27](=[O:29])[C:26]1[CH:30]=[CH:31][C:23]([C:20]2[CH:21]=[N:22][C:17]3[N:18]([C:14]([C:11]4([C:7]5[CH:6]=[C:5]6[C:10](=[CH:9][CH:8]=5)[N:1]=[CH:2][CH:3]=[CH:4]6)[CH2:13][CH2:12]4)=[N:15][N:16]=3)[N:19]=2)=[CH:24][CH:25]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 592163304-[3-(1-Quinolin-6-ylcyclopropyl)[1,2,4]triazolo[4,3-b][1,2,4]triazin-6-yl]benzoic acidHCID 66813129N-methyl-N-pyridin-2-ylethane-1,2-diamine trifluoroacetate

Product 1

HCID 59216296N-methyl-N-2-[methyl(pyridin-2-yl)-amino]ethyl-4-[3-(1-quinolin-6-ylcyclopropyl)[1,2,4]triazolo[4,3-b][1,2,4]triazin-6-yl]benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-[3-(1-quinolin-6-ylcyclopropyl)[1,2,4]triazolo[4,3-b][1,2,4]triazin-6-yl]benzoic acid (10 mg, 0.02 mmol), N-methyl-N-pyridin-2-ylethane-1,2-diamine trifluoroacetate (6.1 mg, 0.037 mmol), benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (13 mg, 0.029 mmol), and N,N-diisopropylethylamine (13 μL, 0.073 mmol) in methylene chloride (0.5 mL) was stirred at RT for 2 h. The solvent was evaporated. The residue was dissolved in methanol, and purified by RP-HPLC (pH=10) to afford the desired product. Analytical LCMS: (M+H)+=556.2.

Workup

  1. customThe solvent was evaporated
  2. dissolutionThe residue was dissolved in methanol
  3. custompurified by RP-HPLC (pH=10)

Sources & evidence

ORD record
ord-d9bd5306e0e0402289bcd5abc282d395
Source dataset
uspto-grants-2011_03
Patent number
US07915408B2

Reaction notes

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