Trifluoroacetic acid → HCID 66711924, compound

HRID 1262216Notes

Reaction equation

HRID 1262216 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21]3[N:26]=[CH:25][C:24]4=[CH:27][CH:28]=[C:29]([C:30]5[CH:35]=[CH:34][CH:33]=[C:32]([S:36](=[O:43])(=[O:42])[NH:37][C:38]([CH3:41])([CH3:40])[CH3:39])[CH:31]=5)[N:23]4[N:22]=3)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[C:38]([NH:37][S:36]([C:32]1[CH:33]=[CH:34][CH:35]=[C:30]([C:29]2[N:23]3[C:24]([CH:25]=[N:26][C:21]([NH:20][C:17]4[CH:18]=[CH:19][C:14]([CH:11]5[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]5)=[CH:15][CH:16]=4)=[N:22]3)=[CH:27][CH:28]=2)[CH:31]=1)(=[O:43])=[O:42])([CH3:41])([CH3:39])[CH3:40]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 667117924-{4-[7-(3-tert-Butylsulfamoyl-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino]-phenyl}-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 66711924HCID 66711924, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-{4-[7-(3-tert-Butylsulfamoyl-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino]-phenyl}-piperidine-1-carboxylic acid tert-butyl ester (50.0 mg, 0.0827 mmol) was treated with trifluoroacetic acid (191 uL, 2.48 mmol) in methylene chloride (3.00 mL). The reaction was diluted with DCM (25 mL) and washed with saturated sodium bicarbonate (25 mL). The aqueous layer was extracted with DCM (25 mL) three times and the combined organic layers were dried over sodium sulfate, filtered, and concentrated under reduced pressure to obtain the title compound as an orange foam (40 mg, 96%). LCMS (m/e) 505 (M+H); 1H-NMR (CDCl3, 400 MHz) δ 8.79 (s, 1H), 8.73 (s, 1H), 8.29 (d, 1H, J=7.8 Hz), 7.87 (d, 1H, J=7.8 Hz), 7.62-7.51 (m, 3H), 7.28 (d, 2H, J=8.3 Hz), 7.07 (d, 1H, J=4.8 Hz), 6.92 (bs, 1H), 6.84 (d, 1H, J=4.8 Hz), 4.77-4.57 (m, 1H), 3.01-3.20 (m, 2H), 2.87-2.73 (m, 2H), 2.72-2.59 (m, 1H), 1.94-1.82 (m, 2H), 1.79-1.63 (m, 2H), 1.17 (s, 9H).

Workup

  1. washwashed with saturated sodium bicarbonate (25 mL)
  2. extractionThe aqueous layer was extracted with DCM (25 mL) three times
  3. dry with materialthe combined organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a5fde114c50e4bc8b03952495387eaea
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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