Toluene → 3-[[5-ethyl-6-[4-(1,2,3,4-tetrahydro-1,8-naphthyridin-7-yl)-1-piperidinyl]-4-pyrimidinyl]amino]-N-(2-pyridinyl)alanine

HRID 729755Notes

Reaction equation

HRID 729755 reaction equation
CC([O:5][C:6](=[O:41])[C@H:7]([CH2:15][NH:16][C:17]1[C:22]([CH2:23][CH3:24])=[C:21]([N:25]2[CH2:30][CH2:29][CH:28]([C:31]3[N:40]=[C:39]4[C:34]([CH2:35][CH2:36][CH2:37][NH:38]4)=[CH:33][CH:32]=3)[CH2:27][CH2:26]2)[N:20]=[CH:19][N:18]=1)[NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1)(C)C.FC(F)(F)C(O)=O.ClCCl.CO.O.C(O)(=O)C.C1(C)C=CC=CC=1>ClCCl>[CH2:23]([C:22]1[C:17]([NH:16][CH2:15][C@@H:7]([C:6]([OH:41])=[O:5])[NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)=[N:18][CH:19]=[N:20][C:21]=1[N:25]1[CH2:30][CH2:29][CH:28]([C:31]2[N:40]=[C:39]3[C:34]([CH2:35][CH2:36][CH2:37][NH:38]3)=[CH:33][CH:32]=2)[CH2:27][CH2:26]1)[CH3:24]

Participants

6

Reactant 4

HCID 1140TolueneHCID 6422Trifluoroacetic acidHCID 18914200Dichloromethane methanol acetic acid waterHCID 57832859(1,1-dimethylethyl) 3-[[5-ethyl-6-[4-(1,2,3,4-tetrahydro-1,8-naphthyridin-7-yl)-1-piperidinyl]-4-pyrimidinyl]amino]-N-(2-pyridinyl)alaninate

Product 1

HCID 578328483-[[5-ethyl-6-[4-(1,2,3,4-tetrahydro-1,8-naphthyridin-7-yl)-1-piperidinyl]-4-pyrimidinyl]amino]-N-(2-pyridinyl)alanineYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

13 mg (0.023 mmole) of (1,1-dimethylethyl)3-[[5-ethyl-6-[4-(1,2,3,4-tetrahydro-1,8-naphthyridin-7-yl)-1-piperidinyl]-4-pyrimidinyl]amino]-N-(2-pyridinyl)alaninate in 2 ml of dichloromethane with 0.2 ml of trifluoroacetic acid is stirred at ambient temperature until the starting product disappears according to TLC (silicagel, eluent: CH2Cl2-MeOH-H2O—AcOH 90-10-1-1). Toluene is added and the reaction mixture is evaporated to dryness under reduced pressure (2 kPa). The residue is solubilized in the minimum amount of dichloromethane then poured into diisopropyl ether. The precipitate is filtered. 13 mg (Yield=76% expressed as ditrifluoroacetate) of expected product is obtained in the form of a beige solid.

Workup

  1. customthe reaction mixture is evaporated to dryness under reduced pressure (2 kPa)
  2. additionthen poured into diisopropyl ether
  3. filtrationThe precipitate is filtered

Sources & evidence

ORD record
ord-7d3bb720a0e34e19b9f95989b5d6be3a
Source dataset
uspto-grants-2009_09
Patent number
US07582640B2

Reaction notes

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