Adipic Acid → HCID 178461898, compound

HRID 1192728Notes

Reaction equation

HRID 1192728 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([C@@H:12]([NH:14][C:15]2[N:23]=[CH:22][N:21]=[C:20]3[C:16]=2[N:17]=[CH:18][NH:19]3)[CH3:13])[C:9]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[CH:25]=2)=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]=[N:7]2.[C:31]([OH:40])(=[O:39])[CH2:32][CH2:33][CH2:34][CH2:35][C:36]([OH:38])=[O:37].CCCCCCC>C(O)(C)C>[C:31]([OH:40])(=[O:39])[CH2:32][CH2:33][CH2:34][CH2:35][C:36]([OH:38])=[O:37].[Cl:1][C:2]1[CH:11]=[C:10]([C@@H:12]([NH:14][C:15]2[N:23]=[CH:22][N:21]=[C:20]3[C:16]=2[N:17]=[CH:18][NH:19]3)[CH3:13])[C:9]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[CH:25]=2)=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]=[N:7]2

Participants

5

Reactant 3

HCID 196Adipic AcidHCID 8900HeptaneHCID 178461897HCID 178461897, compound

Product 1

HCID 178461898HCID 178461898, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
30 °C

Procedure

A solution of N-{(1S)-1-[5-chloro-8-(3-fluorophenyl)cinnolin-7-yl]ethyl}-9H-purin-6-amine (10 g, 24 mmol) and hexanedioic acid (7.0 g, 48 mmol) in isopropyl alcohol (240 mL) was heated at 69° C. for 30 min which gave a milky solution. The reaction mixture was treated with heptane (120 mL) and heated for an additional 30 minUTES which gave a clear solution. The solution was cooled to 30° C. slowly and then to room temperature. The solid that precipitated was collected by filtration, rinsed with heptane (100 mL), and dried on the filter under vacuum for 2 d to give the desired product (12 g, 91%) as an off-white solid. LCMS for C21H16ClFN7 (M+H)+: m/z=420.1; Found: 420.3; 1H NMR (500 MHz, DMSO-d6): δ 12.9 (br s, 1H), 12.0 (br s, 2H), 9.47 (d, J=6.0 Hz, 1H), 8.49-8.43 (m, 1H), 8.41-8.31 (m, 1H), 8.25 (d, J=6.0 Hz, 1H), 8.14-8.05 (m, 2H), 7.68-7.55 (m, 2H), 7.37-7.23 (m, 2H), 5.46-5.34 (m, 1H), 2.22-2.17 (m, 4H), 1.52-1.47 (m, 7H).

Workup

  1. customgave a milky solution
  2. temperatureheated for an additional 30 minUTES which
  3. customgave a clear solution
  4. customto room temperature
  5. customThe solid that precipitated
  6. filtrationwas collected by filtration
  7. washrinsed with heptane (100 mL)
  8. customdried on the
  9. filtrationfilter under vacuum for 2 d

Sources & evidence

ORD record
ord-5e856b194c0c4483ba41fa18f2159bc5
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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