N-(2-(p-bromophenoxy)ethyl)pyrrolidine → HCID 59276591, compound

HRID 1472866Notes

Reaction equation

HRID 1472866 reaction equation
[CH:1]1([NH:6][C:7]2[N:12]3[N:13]=[C:14]([NH2:16])[N:15]=[C:11]3[CH:10]=[CH:9][CH:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.Br[C:18]1[CH:31]=[CH:30][C:21]([O:22][CH2:23][CH2:24][N:25]2[CH2:29][CH2:28][CH2:27][CH2:26]2)=[CH:20][CH:19]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.CC(C)([O-])C.[Na+]>CC(N(C)C)=O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].O1CCOCC1>[CH:1]1([NH:6][C:7]2[N:12]3[N:13]=[C:14]([NH:16][C:18]4[CH:19]=[CH:20][C:21]([O:22][CH2:23][CH2:24][N:25]5[CH2:26][CH2:27][CH2:28][CH2:29]5)=[CH:30][CH:31]=4)[N:15]=[C:11]3[CH:10]=[CH:9][CH:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

8

Reactant 4

HCID 70657N-(2-(p-bromophenoxy)ethyl)pyrrolidineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 23676156Sodium t-butoxideHCID 59589689HCID 59589689, compound

Product 1

HCID 59276591HCID 59276591, compound

Reagents, catalysts & solvents 3

HCID 31374DimethylacetamideCatalystHCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
150 °C

Procedure

In a microwave vial, N*5*-cyclopentyl-[1,2,4]triazolo[1,5-a]pyridine-2,5-diamine (0.07 g, 0.322 mmol), 1-(2-(4-bromophenoxy)ethyl)pyrrolidine (0.13 g, 0.483 mmol), bis(dibenzylideneacetone)palladium (0.01 g, 0.016 mmol), xantphos (0.019 g, 0.032 mmol) and sodium tert-butoxide (0.063 g, 0.644 mmol) were added successively. 1,4-Dioxane (1.2 mL) and dimethylacetamide (4 drops) were added and the vial was sealed and heated under microwave irradiation (150° C., 10 min). The mixture was filtered and purified by preparatory HPLC. LCMS Method: 2: RT: 2.51 min, MI: 407 [M+1]. NMR 1H (DMSO): 1.55-1.75 (m, 10H), 2.03-2.08 (m, 2H), 2.55-2.65 (m, 4H), 2.84 (t, 2H), 3.93-4.00 (m, 1H), 4.01 (t, 2H), 6.10 (d, 1H), 6.15 (d, 1H), 6.69 (d, 1H), 6.87 (d, 2H), 7.37 (t, 1H), 7.63 (d, 2H), 9.17 (s, 1H).

Workup

  1. customthe vial was sealed
  2. filtrationThe mixture was filtered
  3. custompurified by preparatory HPLC

Sources & evidence

ORD record
ord-26f9b36daf1443028665c13b48f382a0
Source dataset
uspto-grants-2015_04
Patent number
US09012633B2

Reaction notes

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