Trifluoroacetic acid → HCID 67545635, compound

HRID 1619801Notes

Reaction equation

HRID 1619801 reaction equation
[F:1][CH:2]([F:49])[C:3]1[N:7]([C:8]2[N:13]=[C:12]([N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[N:11]=[C:10]([N:20]([CH2:34][CH2:35][CH2:36][N:37]3[CH2:42][CH2:41][O:40][CH2:39][CH2:38]3)[CH:21]3[CH2:26][CH2:25][CH2:24][N:23](C(OC(C)(C)C)=O)[CH2:22]3)[N:9]=2)[C:6]2[CH:43]=[CH:44][CH:45]=[C:46]([O:47][CH3:48])[C:5]=2[N:4]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:49][CH:2]([F:1])[C:3]1[N:7]([C:8]2[N:13]=[C:12]([N:14]3[CH2:15][CH2:16][O:17][CH2:18][CH2:19]3)[N:11]=[C:10]([N:20]([CH2:34][CH2:35][CH2:36][N:37]3[CH2:38][CH2:39][O:40][CH2:41][CH2:42]3)[CH:21]3[CH2:26][CH2:25][CH2:24][NH:23][CH2:22]3)[N:9]=2)[C:6]2[CH:43]=[CH:44][CH:45]=[C:46]([O:47][CH3:48])[C:5]=2[N:4]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66698103HCID 66698103, compound

Product 1

HCID 67545635HCID 67545635, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Reaction of tert-butyl 3-{[4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-yl][3-(4-morpholinyl)propyl]amino}-1-piperidinecarboxylate with TFA in CH2Cl2 gave 4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-N-[3-(4-morpholinyl)propyl]-N-(3-piperidinyl)-1,3,5-triazin-2-amine, which was treated with methanesulfonyl chloride in CH2Cl2 to give 4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-N-[1-(methylsulfonyl)-3-piperidinyl]-6-(4-morpholinyl)-N-[3-(4-morpholinyl)propyl]-1,3,5-triazin-2-amine in 78% yield.

Sources & evidence

ORD record
ord-dfabe0066b714e6fb6bbfe4a2c9409d2
Source dataset
uspto-grants-2014_07
Patent number
US08772287B2

Reaction notes

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