4-Methoxybenzoic Acid → HCID 57600250, compound

HRID 1664595Notes

Reaction equation

HRID 1664595 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[N:8]2[C:9](=[O:22])[C:10]3[NH:11][C:12]([Br:21])=[N:13][C:14]=3[N:15]([CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[C:7]2=[N:6][N:5]=1.[CH3:23][O:24][C:25]1[CH:33]=[CH:32][C:28]([C:29](O)=[O:30])=[CH:27][CH:26]=1.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)CC)C>CN(C=O)C.O.C(#N)C>[Br:21][C:12]1[NH:11][C:10]2[C:9](=[O:22])[N:8]3[C:4]([CH2:3][CH2:2][NH:1][C:29](=[O:30])[C:28]4[CH:32]=[CH:33][C:25]([O:24][CH3:23])=[CH:26][CH:27]=4)=[N:5][N:6]=[C:7]3[N:15]([CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[C:14]=2[N:13]=1

Participants

8

Reactant 4

HCID 74784-Methoxybenzoic AcidHCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 57600276HCID 57600276, compound

Product 1

HCID 57600250HCID 57600250, compoundYield 73%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 3-(2-aminoethyl)-7-bromo-9-pentyl-6,9-dihydro-5H-[1,2,4]triazolo[4,3-a]purin-5-one (70 mg, 0.20 mmol), 4-methoxybenzoic acid (32 mg, 0.21 mmol), benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (92 mg, 0.21 mmol), and triethylamine (0.053 mL, 0.38 mmol) in DMF (5 mL) was stirred at room temperature overnight. The reaction mixture was diluted with water and acetonitrile and then purified by prep LCMS to give the desired product (70 mg, 73% yield). LCMS calculated for C21H25BrN7O3 (M+H): 502.1, 504.0. found: 502.0, 504.0.

Workup

  1. custompurified by prep LCMS

Sources & evidence

ORD record
ord-f0884906294e4de4924489f945f34257
Source dataset
uspto-grants-2011_10
Patent number
US08039478B2

Reaction notes

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