Toluene → HCID 57832870, compound

HRID 2358214Notes

Reaction equation

HRID 2358214 reaction equation
[CH2:1]([C:3]1[C:4]([NH:25][CH2:26][C@@H:27]([C:43]([O:45]C(C)(C)C)=[O:44])[NH:28][C:29]([O:31][CH2:32][C:33]23[CH2:42][CH:37]4[CH2:38][CH:39]([CH2:41][CH:35]([CH2:36]4)[CH2:34]2)[CH2:40]3)=[O:30])=[N:5][CH:6]=[N:7][C:8]=1[N:9]1[CH2:14][CH2:13][CH:12]([C:15]2[N:24]=[C:23]3[C:18]([CH2:19][CH2:20][CH2:21][NH:22]3)=[CH:17][CH:16]=2)[CH2:11][CH2:10]1)[CH3:2].FC(F)(F)C(O)=O.ClCCl.CO.O.C(O)(=O)C.C1(C)C=CC=CC=1>ClCCl>[CH2:1]([C:3]1[C:4]([NH:25][CH2:26][C@@H:27]([C:43]([OH:45])=[O:44])[NH:28][C:29]([O:31][CH2:32][C:33]23[CH2:34][CH:35]4[CH2:41][CH:39]([CH2:38][CH:37]([CH2:36]4)[CH2:42]2)[CH2:40]3)=[O:30])=[N:5][CH:6]=[N:7][C:8]=1[N:9]1[CH2:10][CH2:11][CH:12]([C:15]2[N:24]=[C:23]3[C:18]([CH2:19][CH2:20][CH2:21][NH:22]3)=[CH:17][CH:16]=2)[CH2:13][CH2:14]1)[CH3:2]

Participants

6

Reactant 4

HCID 1140TolueneHCID 6422Trifluoroacetic acidHCID 18914200Dichloromethane methanol acetic acid waterHCID 57832876HCID 57832876, compound

Product 1

HCID 57832870HCID 57832870, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

130 mg (0.19 mmoles) 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-[(adamantylmethoxy)carbonyl]alaninate in 20 ml of dichloromethane with 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 with a little methanol then poured into diisopropyl ether. The precipitate is filtered. 368 mg (Yield=61% expressed as ditrifluoroacetate) of expected product is obtained in the form of an amorphous 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-7c95075902084db0862b60f86ad73d9b
Source dataset
uspto-grants-2010_07
Patent number
US07763621B2

Reaction notes

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