Toluene → HCID 86639120, compound

HRID 2261174Notes

Reaction equation

HRID 2261174 reaction equation
[CH2:1]([C:3]1[C:4]([NH:25][CH2:26][CH:27]([NH:35][C:36]([NH:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=2[N+:45]([O-:47])=[O:46])=[O:37])[C:28]([O:30]C(C)(C)C)=[O:29])=[N:5][CH:6]=[N:7][C:8]=1[N:9]1[CH2:14][CH2:13][CH:12]([C:15]2[CH:24]=[CH:23][C:22]3[CH2:21][CH2:20][CH2:19][NH:18][C:17]=3[N:16]=2)[CH2:11][CH2:10]1)[CH3:2].[F:48][C:49]([F:54])([F:53])[C:50]([OH:52])=[O:51].ClCCl.CO.O.C(O)(=O)C.C1(C)C=CC=CC=1>ClCCl>[F:48][C:49]([F:54])([F:53])[C:50]([OH:52])=[O:51].[F:48][C:49]([F:54])([F:53])[C:50]([OH:52])=[O:51].[CH2:1]([C:3]1[C:4]([NH:25][CH2:26][CH:27]([NH:35][C:36]([NH:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=2[N+:45]([O-:47])=[O:46])=[O:37])[C:28]([OH:30])=[O:29])=[N:5][CH:6]=[N:7][C:8]=1[N:9]1[CH2:10][CH2:11][CH:12]([C:15]2[CH:24]=[CH:23][C:22]3[CH2:21][CH2:20][CH2:19][NH:18][C:17]=3[N:16]=2)[CH2:13][CH2:14]1)[CH3:2]

Participants

6

Reactant 4

HCID 1140TolueneHCID 6422Trifluoroacetic acidHCID 18914200Dichloromethane methanol acetic acid waterHCID 66641088HCID 66641088, compound

Product 1

HCID 86639120HCID 86639120, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

30 mg (0.046 mmole) of tert-butyl 3-[5-ethyl-6-[4-(5,6,7,8-tetrahydro-(1,8)naphthyridin-2-yl)-piperidin-1-yl]-pyrimidin-4-ylamino]-2-[3-(2-nitrophenyl)-ureido]-propionate in 3 ml of dichloromethane with 0.5 ml of trifluoroacetic acid is stirred at ambient temperature until the starting product disappears according to TLC (silica gel, 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. 35 mg of expected product is obtained in the form of a yellow 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-268f6c95e7e94d70a21668013a93b9aa
Source dataset
uspto-grants-2010_12
Patent number
US07846932B2

Reaction notes

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