Triethylamine → HCID 135916071, compound

HRID 2172890Notes

Reaction equation

HRID 2172890 reaction equation
[NH2:1][C:2]1[NH:3][C:4](=[O:16])[C:5]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][C:12]=3[Cl:14])[NH:7][C:6]=2[N:15]=1.[CH3:17][C:18]1[CH:23]=CN=C(N)[C:19]=1C.C(N(CC)CC)C.C(Cl)(Cl)Cl.[CH3:37][OH:38]>>[Cl:14][C:12]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:13]=1[C:5]1[C:37](=[O:38])[NH:1][C:2]([NH:3][C:4](=[O:16])[C:18]([CH3:23])([CH3:19])[CH3:17])=[N:15][C:6]=1[NH:7]2

Participants

5

Reactant 4

HCID 8471TriethylamineHCID 110078842-Amino-3,4-dimethylpyridineHCID 21584188Chloroform methanolHCID 1357418862-Amino-5-chloro-3H-pyrimido[4,5-B]indol-4(9H)-one

Product 1

HCID 135916071HCID 135916071, compoundYield 40%

Procedure

Compound 8 (300 mg, 1.27 mmol), 2-dimethyl propanoic anhydride (713.32 mg, 3.83 mmol), dimethyl aminopyridine (7 mg, 0.06 mmol), triethylamine (514.05 mg, 5.08 mmol) were weighed together in a 50 mL round bottom flask. This flask was placed in an oil bath at 60° C. with stirring for 2 days. Then, to the reaction mixture was added 1 g silica gel. The DMF was removed using oil pump and a silica gel plug was made. The plug was transferred on top of a column packed with silica gel, twenty times the weight of plug, eluted with chloroform, 1% methanol in chloroform and 5% methanol in chloroform. Fractions containing the product 9 (TLC) were pooled and evaporated to give solid compound. The overall yield was 40%. TLC Rf 0.45 (chloroform-methanol 10:1), m.p. 185.8-190.1° C., 1H NMR: δ 1.27 (s, 9H, pivaloyl); 7.19-7.40 (m, 3H, phenyl); 11.15 (s, 1H, 9-NH, exch); 11.94 (s, 1H, 9-NH, exch); 12.12 (s, 1H, 3-NH, exch).

Workup

  1. customThis flask was placed in an oil bath at 60° C.
  2. additionThen, to the reaction mixture was added 1 g silica gel
  3. customThe DMF was removed
  4. washeluted with chloroform, 1% methanol in chloroform and 5% methanol in chloroform
  5. additionFractions containing the product 9 (TLC)
  6. customevaporated
  7. customto give solid compound

Sources & evidence

ORD record
ord-38e0a510381641849d09c1218e5b432c
Source dataset
uspto-grants-2015_06
Patent number
US09056869B2

Reaction notes

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