Triphenylphosphine → Methyl 2-(6-(tert-butoxycarbonylamino)hexyloxy)-4-(4-chloro-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)benzoate

HRID 400359Notes

Reaction equation

HRID 400359 reaction equation
[Cl:1][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]([OH:25])[CH:16]=2)[N:3]=1.O[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][NH:33][C:34](=[O:40])[O:35][C:36]([CH3:39])([CH3:38])[CH3:37].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C(Cl)Cl>[C:36]([O:35][C:34]([NH:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][O:25][C:17]1[CH:16]=[C:15]([NH:14][C:4]2[N:3]=[C:2]([Cl:1])[N:7]=[C:6]([O:8][CH2:9][C:10]([F:12])([F:13])[F:11])[N:5]=2)[CH:24]=[CH:23][C:18]=1[C:19]([O:21][CH3:22])=[O:20])=[O:40])([CH3:39])([CH3:38])[CH3:37]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 4146612tert-Butyl N-(6-hydroxyhexyl)carbamateHCID 5363146Diisopropyl azodicarboxylateHCID 86664101Methyl 4-(4-chloro-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)-2-hydroxybenzoate

Product 1

HCID 86664100Methyl 2-(6-(tert-butoxycarbonylamino)hexyloxy)-4-(4-chloro-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)benzoateYield 36%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

methyl 4-(4-chloro-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)-2-hydroxybenzoate (100 mg, 0.264 mmol), tert-butyl 6-hydroxyhexylcarbamate (68.9 mg, 0.317 mmol), Triphenylphosphine (139 mg, 0.528 mmol), were dissolved in DCM then DIAD (0.103 mL, 0.528 mmol) was added. The reaction was stirred for 16 h. The solvent was removed under vacuum and the crude product was purified by silica gel chromatography using 20% EtOAc/Hexanes. The product fractions were collected and the solvent was removed under vacuum to give 55 mg (36%) methyl 2-(6-(tert-butoxycarbonylamino)hexyloxy)-4-(4-chloro-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)benzoate.

Workup

  1. customThe solvent was removed under vacuum
  2. customthe crude product was purified by silica gel chromatography
  3. customThe product fractions were collected
  4. customthe solvent was removed under vacuum

Sources & evidence

ORD record
ord-71fd19f5bc3d4f2db17b3f9229728784
Source dataset
uspto-grants-2014_06
Patent number
US08741884B2

Reaction notes

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