4-Methoxypiperidine → N-(4-(7-methoxy-1,5-naphthyridin-4-ylthio)phenyl)-4-(4-methoxypiperidin-1-yl)phthalazin-1-amine

HRID 503523Notes

Reaction equation

HRID 503523 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([S:19][C:20]3[C:29]4[C:24](=[CH:25][C:26]([O:30][CH3:31])=[CH:27][N:28]=4)[N:23]=[CH:22][CH:21]=3)=[CH:15][CH:14]=2)=[N:4][N:3]=1.[CH3:32][O:33][CH:34]1[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]1>CS(C)=O.CO>[CH3:31][O:30][C:26]1[CH:25]=[C:24]2[C:29]([C:20]([S:19][C:16]3[CH:17]=[CH:18][C:13]([NH:12][C:5]4[C:6]5[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=5)[C:2]([N:37]5[CH2:38][CH2:39][CH:34]([O:33][CH3:32])[CH2:35][CH2:36]5)=[N:3][N:4]=4)=[CH:14][CH:15]=3)=[CH:21][CH:22]=[N:23]2)=[N:28][CH:27]=1

Participants

5

Reactant 2

HCID 776664-MethoxypiperidineHCID 866286644-chloro-N-(4-(7-methoxy-1,5-naphthyridin-4-ylthio)phenyl)phthalazin-1-amine

Product 1

HCID 59427357N-(4-(7-methoxy-1,5-naphthyridin-4-ylthio)phenyl)-4-(4-methoxypiperidin-1-yl)phthalazin-1-amine

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolvent

Procedure

A 15 ml sealed pressure tube was charged with 4-chloro-N-(4-(7-methoxy-1,5-naphthyridin-4-ylthio)phenyl)phthalazin-1-amine (120 mg, 0.269 mmol) and 4-methoxypiperidine (620 mg, 5.382 mmol), in 0.3 ml of DMSO. The sealed tube was placed in a preheated oil bath at 100° C. where it was stirred for 16 hours. The reaction was cooled to ambient temperature, diluted with 2 ml of MeOH, and the solution purified using Gilson Reverse Phase HPLC. The fractions containing the desired product was neutralized with saturated sodium bicarbonate and extracted with 10 ml of DCM (3×). The organics were dried over Na2SO4, filtered and the filtrate was concentrated in vacuo to afford N-(4-(7-methoxy-1,5-naphthyridin-4-ylthio)phenyl)-4-(4-methoxypiperidin-1-yl)phthalazin-1-amine as a yellow solid. MS [M+H]+=525.

Workup

  1. customA 15 ml sealed pressure tube
  2. customThe sealed tube was placed in a preheated oil bath at 100° C.
  3. customthe solution purified
  4. additionThe fractions containing the desired product
  5. extractionextracted with 10 ml of DCM (3×)
  6. dry with materialThe organics were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-4d045b3f597c4b5098e2026baffb5173
Source dataset
uspto-grants-2010_08
Patent number
US07776857B2

Reaction notes

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