Tert-butyl (8-aminooctyl)carbamate → Methyl 4-(4-(8-(tert-butoxycarbonylamino)octylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)-2-(3-chloropropoxy)benzoate

HRID 400362Notes

Reaction equation

HRID 400362 reaction equation
Cl[C:2]1[N:7]=[C:6]([O:8][CH2:9][C:10]([F:13])([F:12])[F:11])[N:5]=[C:4]([NH:14][C:15]2[CH:24]=[CH:23][C:18]([C:19]([O:21][CH3:22])=[O:20])=[C:17]([O:25][CH2:26][CH2:27][CH2:28][Cl:29])[CH:16]=2)[N:3]=1.[NH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][NH:39][C:40](=[O:46])[O:41][C:42]([CH3:45])([CH3:44])[CH3:43]>C1COCC1.C(Cl)Cl>[C:42]([O:41][C:40]([NH:39][CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][NH:30][C:2]1[N:7]=[C:6]([O:8][CH2:9][C:10]([F:13])([F:12])[F:11])[N:5]=[C:4]([NH:14][C:15]2[CH:24]=[CH:23][C:18]([C:19]([O:21][CH3:22])=[O:20])=[C:17]([O:25][CH2:26][CH2:27][CH2:28][Cl:29])[CH:16]=2)[N:3]=1)=[O:46])([CH3:45])([CH3:44])[CH3:43]

Participants

5

Reactant 2

HCID 4086223Tert-butyl (8-aminooctyl)carbamateHCID 86664102Methyl 4-((4-chloro-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl)amino)-2-(3-chloropropoxy)benzoate

Product 1

HCID 67283231Methyl 4-(4-(8-(tert-butoxycarbonylamino)octylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)-2-(3-chloropropoxy)benzoateYield 96%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 4-((4-chloro-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl)amino)-2-(3-chloropropoxy)benzoate (200 mg, 0.439 mmol) in THF (2 mL) was added tert-butyl (8-aminooctyl)carbamate (118 mg, 0.483 mmol) and Hunig'sBase (230 μl, 1.318 mmol). The resulting mixture was stirred for 16 h. The mixture was diluted with DCM and washed with water, then brine. The organic layer was collected, dried over sodium sulfate, and concentrated under vacuum. The crude product was purified by silica gel chromatography using a gradient of 20-40% EtOAc/hexanes. The product fractions were collected and the solvent removed under vacuum to give 208 mg (96%) methyl 4-(4-(8-(tert-butoxycarbonylamino)octylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)-2-(3-chloropropoxy)benzoate.

Workup

  1. washwashed with water
  2. customThe organic layer was collected
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under vacuum
  5. customThe crude product was purified by silica gel chromatography
  6. customThe product fractions were collected
  7. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-ca81f0c30db0448990aed0b1c816e612
Source dataset
uspto-grants-2014_06
Patent number
US08741884B2

Reaction notes

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