Trifluoroacetic acid → (S)-methyl 3-amino-2-(4-(4-(1-(4-chlorophenyl)cyclopropylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)benzamido)propanoate

HRID 1407037Notes

Reaction equation

HRID 1407037 reaction equation
C(OC([NH:8][CH2:9][C@H:10]([NH:15][C:16](=[O:47])[C:17]1[CH:22]=[CH:21][C:20]([NH:23][C:24]2[N:29]=[C:28]([NH:30][C:31]3([C:34]4[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][CH:35]=4)[CH2:33][CH2:32]3)[N:27]=[C:26]([O:41][CH2:42][C:43]([F:46])([F:45])[F:44])[N:25]=2)=[CH:19][CH:18]=1)[C:11]([O:13][CH3:14])=[O:12])=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:8][CH2:9][C@H:10]([NH:15][C:16](=[O:47])[C:17]1[CH:22]=[CH:21][C:20]([NH:23][C:24]2[N:29]=[C:28]([NH:30][C:31]3([C:34]4[CH:35]=[CH:36][C:37]([Cl:40])=[CH:38][CH:39]=4)[CH2:32][CH2:33]3)[N:27]=[C:26]([O:41][CH2:42][C:43]([F:46])([F:45])[F:44])[N:25]=2)=[CH:19][CH:18]=1)[C:11]([O:13][CH3:14])=[O:12]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68182808(S)-methyl 3-(tert-butoxycarbonylamino)-2-(4-(4-(1-(4-chlorophenyl)cyclopropylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)benzamido)propanoate

Product 1

HCID 86691671(S)-methyl 3-amino-2-(4-(4-(1-(4-chlorophenyl)cyclopropylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)benzamido)propanoateYield 93.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-methyl 3-(tert-butoxycarbonylamino)-2-(4-(4-(1-(4-chlorophenyl)cyclopropylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)benzamido)propanoate (1 g) in CH2Cl2 (10 mL) was added TFA (3 mL). The mixture was stirred at room temperature for 16 hours. All the solvents were removed under vacuum to give (S)-methyl 3-amino-2-(4-(4-(1-(4-chlorophenyl)cyclopropylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)benzamido)propanoate (0.8 g).

Workup

  1. customAll the solvents were removed under vacuum

Sources & evidence

ORD record
ord-9dd13cd20290418ca92c91549d77e737
Source dataset
uspto-grants-2014_12
Patent number
US08916702B2

Reaction notes

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