Trifluoroacetic acid → HCID 67533983, compound

HRID 1619798Notes

Reaction equation

HRID 1619798 reaction equation
[F:1][CH:2]([F:46])[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]([CH3:39])[CH3:38])[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:40]=[CH:41][CH:42]=[C:43]([O:44][CH3:45])[C:5]=2[N:4]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:46][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]([CH:21]3[CH2:26][CH2:25][CH2:24][NH:23][CH2:22]3)[CH2:34][CH2:35][CH2:36][N:37]([CH3:39])[CH3:38])[N:9]=2)[C:6]2[CH:40]=[CH:41][CH:42]=[C:43]([O:44][CH3:45])[C:5]=2[N:4]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66698080HCID 66698080, compound

Product 1

HCID 67533983HCID 67533983, compoundYield 88.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 3-{[4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-yl][3-(dimethylamino)propyl]amino}-1-piperidinecarboxylate (430 mg, 0.67 mmol) in CH2Cl2 (10 mL), was added TFA (5 mL). The resulting mixture was stirred at room temperature for 30 min. The solvent and excess TFA were removed under vacuum. The residue was diluted with water and neutralized with aqueous NH3. The resulting precipitate was filtered, washed with water, and dried to give N-[4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-N3,N3-dimethyl-N1-(3-piperidinyl)-1,3-propanediamine (323 mg, 88%): 1H NMR (DMSO-d6) (rotamers) δ 7.95 and 7.93 (2d, J=9.5, 8.8 Hz, 1H), 7.77 and 7.71 (2t, JHF=53.1 Hz, 1H), 7.42-7.36 (m, 1H), 6.95 (d, J=1 Hz, 1H), 4.55-4.48 and 4.46-4.39 (2m, 1H), 3.98 (s, 3H), 3.81-3.80 (m, 4H), 3.72-3.70 (m, 4H), 3.55-3.45 (m, 2H), 2.99-2.96 (m, 1H), 2.92-2.89 (m, 1H), 2.77-2.66 (m, 1H), 2.45-2.40 (m, 1H), 2.27 (t, J=6.9 Hz, 2H), 2.16 and 2.12 (2s, 6H), 1.80-1.48 (m, 6H).

Workup

  1. customThe solvent and excess TFA were removed under vacuum
  2. additionThe residue was diluted with water and neutralized with aqueous NH3
  3. filtrationThe resulting precipitate was filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-00be82e89e27492f8fbffcd3dba5466d
Source dataset
uspto-grants-2014_07
Patent number
US08772287B2

Reaction notes

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