Benzoic Acid → HCID 57600295, compound

HRID 2368609Notes

Reaction equation

HRID 2368609 reaction equation
Cl.[NH2:2][CH2:3][C:4]1[N:8]2[C:9](=[O:21])[C:10]3[NH:11][CH:12]=[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.[C:22](O)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=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:21]=[C:9]1[N:8]2[C:4]([CH2:3][NH:2][C:22](=[O:29])[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[N:5][N:6]=[C:7]2[N:15]([CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[C:14]2[N:13]=[CH:12][NH:11][C:10]1=2

Participants

6

Reactant 4

HCID 243Benzoic AcidHCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 66725663HCID 66725663, compound

Product 1

HCID 57600295HCID 57600295, compoundYield 77.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The mixture of 3-(aminomethyl)-9-pentyl-6,9-dihydro-5H-[1,2,4]triazolo[4,3-a]purin-5-one hydrochloride (160 mg, 0.51 mmol), [B] benzoic Acid (0.069 g, 0.56 mmol), benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (0.25 g, 0.56 mmol) and triethylamine (0.21 mL, 1.5 mmol) in DMF (10 mL) was stirred at room temperature overnight. The reaction mixture was purified by preparative LCMS to yield the desired product (150 mg, 77%). LCMS calculated for C19H22N7O2 (M+H): 380.2. Found: 380.2.

Workup

  1. customThe reaction mixture was purified by preparative LCMS

Sources & evidence

ORD record
ord-e7ee98f59bb54583b6f8bd7668e439d2
Source dataset
uspto-grants-2014_04
Patent number
US08703783B2

Reaction notes

Loading…