Triethylamine → HCID 178519693, compound

HRID 931184Notes

Reaction equation

HRID 931184 reaction equation
[Cl:1][C:2]1[CH:12]=[CH:11][C:5]([O:6][CH2:7][C:8](O)=O)=[CH:4][CH:3]=1.[NH2:13][C:14]1[CH:15]=[CH:16][C:17]([N:21]2[CH2:26][CH2:25][CH2:24][C@@H:23]([C:27]([N:29]3[CH2:33][CH2:32][CH2:31][CH2:30]3)=[O:28])[CH2:22]2)=[N:18][C:19]=1[NH2:20].O1CCOCC1.C(N(CC)CC)C.CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH2:7][C:8]2[NH:20][C:19]3=[N:18][C:17]([N:21]4[CH2:26][CH2:25][CH2:24][CH:23]([C:27]([N:29]5[CH2:33][CH2:32][CH2:31][CH2:30]5)=[O:28])[CH2:22]4)=[CH:16][CH:15]=[C:14]3[N:13]=2)=[CH:11][CH:12]=1

Participants

6

Reactant 5

HCID 8471TriethylamineHCID 26229(4-Chlorophenoxy)acetic acidHCID 312751,4-DioxaneHCID 111923Propylphosphonic anhydrideHCID 89854052(R)-(1-(5,6-diaminopyridin-2-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanone

Product 1

HCID 178519693HCID 178519693, compound

Conditions

Temperature
140 °C

Procedure

2-(4-Chlorophenoxy)acetic acid (75 μmol) was added into an 8-mL vial followed by a solution of (R)-(1-(5,6-diaminopyridin-2-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanone in anhydrous dioxane (600 μL, 127.5 μmol, 0.21M). Triethylamine (90 μL, 648 μmol) and 1-propanephosphonic acid cyclic anhydride (120 μL, 50% in ethyl acetate, 202 μmol) were added. The vial was capped and the reaction mixture was shaken at 140° C. for 16 h. The solvent was removed by Speedvac and the residue was purified via HPLC to afford the title compound. MS API-ES+ (M+H) 440; HPLC retention time 2.473 min (Method D).

Workup

  1. customThe vial was capped
  2. customThe solvent was removed by Speedvac
  3. customthe residue was purified via HPLC

Sources & evidence

ORD record
ord-7d9b01f878a342b091b7aa5e731111f2
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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