Trifluoroacetic acid → HCID 19599752, compound

HRID 609659Notes

Reaction equation

HRID 609659 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][N:10]([CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH2:11][CH2:12][CH2:13][C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([N:23]3[CH:27]=[N:26][N:25]=[CH:24]3)[CH:21]=2)[NH:16][CH:15]=1)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[C:29]1([CH2:28][N:10]([CH2:11][CH2:12][CH2:13][C:14]2[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([N:23]4[CH:27]=[N:26][N:25]=[CH:24]4)[CH:21]=3)[NH:16][CH:15]=2)[CH2:9][CH2:8][NH2:7])[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67575036HCID 67575036, compound

Product 1

HCID 19599752HCID 19599752, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-[(phenylmethyl)(3-[5-(1,2,4-triazol-4-yl)-1H-indol-3-yl]propyl)amino]ethyl carbamic acid tert-butyl ester (440 mg, 0.93 mmol) and trifluoroacetic acid (3 ml) in CH2Cl2 (20 ml) was stirred at room temperature for 5 h. After this time the solvent was evaporated and the residue azeotroped with CH2Cl2 (20 ml) and toluene (20 ml). The residue was partitioned between CH2Cl2 (2×30 ml) and K2CO3 (10%; 20 ml). the combined organic layers were dried (NaSO4) and evaporated. The amine (287 mg, 83%, which was isolated as a colourless foam was used without further purification. 1H NMR (250 MHz, CDCl3 +d4 -MeOH) δ1.83-1.99 (2H, m), 2.44-2.59 (4H, m), 2.61-2.79 (4H, m) 3.58 (2H, s), 7.07 (1H, s), 7.11 (1H, dd, J=8.6 and 2.1 Hz), 7.20-7.32 (5H, m), 7.48 (1H, d, J=8.6 Hz), 7.51 (1H, d, J=2.1 Hz), 8.49 (2H, s).

Workup

  1. customAfter this time the solvent was evaporated
  2. customthe residue azeotroped with CH2Cl2 (20 ml) and toluene (20 ml)
  3. customThe residue was partitioned between CH2Cl2 (2×30 ml) and K2CO3 (10%; 20 ml)
  4. dry with materialthe combined organic layers were dried (NaSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-2cbad70f56534ea0b6f5d7523f5253e1
Source dataset
uspto-grants-1999_12
Patent number
US05998415

Reaction notes

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