Trifluoroacetic acid → Methyl 4-(4-(8-aminooctylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)-2-(3-chloropropoxy)benzoate

HRID 400363Notes

Reaction equation

HRID 400363 reaction equation
C(OC([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][NH:17][C:18]1[N:23]=[C:22]([O:24][CH2:25][C:26]([F:29])([F:28])[F:27])[N:21]=[C:20]([NH:30][C:31]2[CH:40]=[CH:39][C:34]([C:35]([O:37][CH3:38])=[O:36])=[C:33]([O:41][CH2:42][CH2:43][CH2:44][Cl:45])[CH:32]=2)[N:19]=1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][NH:17][C:18]1[N:23]=[C:22]([O:24][CH2:25][C:26]([F:29])([F:28])[F:27])[N:21]=[C:20]([NH:30][C:31]2[CH:40]=[CH:39][C:34]([C:35]([O:37][CH3:38])=[O:36])=[C:33]([O:41][CH2:42][CH2:43][CH2:44][Cl:45])[CH:32]=2)[N:19]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67283231Methyl 4-(4-(8-(tert-butoxycarbonylamino)octylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)-2-(3-chloropropoxy)benzoate

Product 1

HCID 67283857Methyl 4-(4-(8-aminooctylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)-2-(3-chloropropoxy)benzoateYield 120.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

methyl 4-((4-((8-((tert-butoxycarbonyl)amino)octyl)amino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl)amino)-2-(3-chloropropoxy)benzoate (280 mg, 0.422 mmol) was dissolved in TFA (1 mL, 12.98 mmol) and DCM (2 mL). The reaction was stirred for 1 h. The solvent was removed under vacuum to give 286 mg (100%) methyl 4-(4-(8-aminooctylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)-2-(3-chloropropoxy)benzoate, TFA which was used in the next step without further purification.

Workup

  1. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-f2c8afcd3e8d48098a07d2649ff36dfd
Source dataset
uspto-grants-2014_06
Patent number
US08741884B2

Reaction notes

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