Triethylamine → HCID 89714528, compound

HRID 2273080Notes

Reaction equation

HRID 2273080 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:18]3[C:17](=[O:19])[N:16]([CH3:20])[CH2:15][C:14]([CH3:22])([CH3:21])[O:13][C:12]=3[N:11]=[C:10]([N:23]3[CH2:29][CH:28]4[O:30][CH:25]([CH2:26][CH2:27]4)[CH2:24]3)[N:9]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl[C:39](Cl)([O:41]C(=O)OC(Cl)(Cl)Cl)Cl.[NH2:50][C:51]1[CH:56]=[C:55]([O:57][CH3:58])[CH:54]=[CH:53][N:52]=1>C(Cl)Cl.C(Cl)Cl.CO.CCCCC>[CH3:58][O:57][C:55]1[CH:54]=[CH:53][N:52]=[C:51]([NH:50][C:39]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([C:8]3[C:18]4[C:17](=[O:19])[N:16]([CH3:20])[CH2:15][C:14]([CH3:22])([CH3:21])[O:13][C:12]=4[N:11]=[C:10]([N:23]4[CH2:24][CH:25]5[O:30][CH:28]([CH2:27][CH2:26]5)[CH2:29]4)[N:9]=3)=[CH:6][CH:7]=2)=[O:41])[CH:56]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 108987152-Amino-4-MethoxypyridineHCID 89714608HCID 89714608, compound

Product 1

HCID 89714528HCID 89714528, compoundYield 29.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 22051252HCID 22051252, compoundSolvent

Procedure

210 mg (0.51 mmol) of 4-(4-aminophenyl)-6,8,8-trimethyl-2-(8-oxa-3-azabicyclo[3.2.1]oct-3-yl)-7,8-dihydro-6H-9-oxa-1,3,6-triazabenzocyclohepten-5-one and 314.5 mg (3 mmol) of triethylamine are added to 3 ml of DCM. This mixture is then added under nitrogen to a solution containing 152.2 mg (0.51 mmol) of triphosgene in 3 ml of DCM. The mixture is stirred at room temperature for 30 minutes, and 268.1 mg (2 mmol) of 2-amino-4-methoxypyridine are then added. This mixture is stirred for 2 hours at room temperature, extracted with DCM, washed once with water and then with saturated NaCl solution, and the organic phase is dried over Na2SO4. The resulting phase is filtered and the filtrate is evaporated under reduced pressure. The residue is chromatographed on silica gel, eluting with a DCM/MeOH mixture from (100/0 v/v) up to (100/4 v/v). The solid obtained is then taken up in a DCM/MeOH/pentane mixture, filtered off and dried to give 85 mg of 1-(4-methoxypyridin-2-yl)-3-{4-[6,8,8-trimethyl-2-(8-oxa-3-azabicyclo[3.2.1]oct-3-yl)-5-oxo-5,6,7,8-tetrahydro-9-oxa-1,3,6-triazabenzocyclohepten-4-yl]phenyl}urea.

Workup

  1. additionThis mixture is then added under nitrogen to a solution
  2. stirringThis mixture is stirred for 2 hours at room temperature
  3. extractionextracted with DCM
  4. washwashed once with water
  5. dry with materialwith saturated NaCl solution, and the organic phase is dried over Na2SO4
  6. filtrationThe resulting phase is filtered
  7. customthe filtrate is evaporated under reduced pressure
  8. customThe residue is chromatographed on silica gel
  9. washeluting with a DCM/MeOH mixture from (100/0 v/v) up to (100/4 v/v)
  10. customThe solid obtained
  11. filtrationfiltered off
  12. customdried

Sources & evidence

ORD record
ord-2babbfc45fb94c59b95100f3e80aa0e3
Source dataset
uspto-grants-2015_09
Patent number
US09120812B2

Reaction notes

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