Toluene → HCID 86639118, compound

HRID 1615948Notes

Reaction equation

HRID 1615948 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH:12]([CH2:20][NH:21][C:22]1[C:27]([CH2:28][CH3:29])=[C:26]([NH:30][CH2:31][CH2:32][CH2:33][C:34]2[CH:43]=[CH:42][C:41]3[CH2:40][CH2:39][CH2:38][NH:37][C:36]=3[N:35]=2)[N:25]=[CH:24][N:23]=1)[C:13]([O:15]C(C)(C)C)=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:44][C:45]([F:50])([F:49])[C:46]([OH:48])=[O:47].C1(C)C=CC=CC=1>ClCCl>[F:44][C:45]([F:50])([F:49])[C:46]([OH:48])=[O:47].[F:44][C:45]([F:50])([F:49])[C:46]([OH:48])=[O:47].[CH2:1]([O:8][C:9]([NH:11][CH:12]([CH2:20][NH:21][C:22]1[C:27]([CH2:28][CH3:29])=[C:26]([NH:30][CH2:31][CH2:32][CH2:33][C:34]2[CH:43]=[CH:42][C:41]3[CH2:40][CH2:39][CH2:38][NH:37][C:36]=3[N:35]=2)[N:25]=[CH:24][N:23]=1)[C:13]([OH:15])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 6422Trifluoroacetic acidHCID 66641325HCID 66641325, compound

Product 1

HCID 86639118HCID 86639118, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

65 mg (0.11 mmole) of tert-butyl 2-benzyloxycarbonylamino-3-[5-ethyl-6-[3-(5,6,7,8-tetrahydro-[1,8]-naphthyridin-2-yl)propylamino]-pyrimidin-4-ylamino]-propionate in 5 ml of dichloromethane with 0.5 ml of trifluoroacetic acid is stirred at ambient temperature for 16 hours. 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. 45 mg 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-802fa720b7c9457695f913b6a4ab4da4
Source dataset
uspto-grants-2014_07
Patent number
US08765766B2

Reaction notes

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