Tetrahydrofuran → Gsk 1034702

HRID 2061506Notes

Reaction equation

HRID 2061506 reaction equation
[NH2:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([CH3:9])=[CH:4][C:3]=1[NH:10][CH:11]1[CH2:16][CH2:15][N:14]([CH:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)[CH2:13][CH2:12]1.[O:23]1CCC[CH2:24]1>>[F:8][C:7]1[C:2]2[NH:1][C:24](=[O:23])[N:10]([CH:11]3[CH2:16][CH2:15][N:14]([CH:17]4[CH2:22][CH2:21][O:20][CH2:19][CH2:18]4)[CH2:13][CH2:12]3)[C:3]=2[CH:4]=[C:5]([CH3:9])[CH:6]=1

Participants

3

Reactant 2

HCID 8028Tetrahydrofuran2×HCID 59683272(2-amino-3-fluoro-5-methylphenyl)[1-(tetrahydro-2H-pyran-4-yl)-4-piperidinyl]amine

Product 1

HCID 16038386Gsk 1034702

Procedure

A mixture of (2-amino-3-fluoro-5-methylphenyl)[1-(tetrahydro-2H-pyran-4-yl)-4-piperidinyl]amine (0.5 g), N,N′-carbonyldiimidazole (0.66 g) and tetrahydrofuran (7 ml) was heated to reflux. After 30 minutes, tetrahydrofuran (3 ml) was added, and the mixture heated at reflux for a further 1½ hours. The reaction mixture was filtered and washed with tetrahydrofuran (10 ml), then the solid was dried at 40-45° C. under high vacuum to give the title compound (0.323 g).

Workup

  1. temperaturewas heated to reflux
  2. temperaturethe mixture heated
  3. temperatureat reflux for a further 1½ hours
  4. filtrationThe reaction mixture was filtered
  5. washwashed with tetrahydrofuran (10 ml)
  6. customthe solid was dried at 40-45° C. under high vacuum

Sources & evidence

ORD record
ord-6255ceaaf91c41eb93f2e8e82578d4a5
Source dataset
uspto-grants-2012_10
Patent number
US08283364B2

Reaction notes

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