Toluene → HCID 86639118, compound

HRID 1094220Notes

Reaction equation

HRID 1094220 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-7af198c5d15f4997ac3756915813040c
Source dataset
uspto-grants-2012_03
Patent number
US08133896B2

Reaction notes

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