Dichloromethane → HCID 86661703, compound

HRID 1262452Notes

Reaction equation

HRID 1262452 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][C:33]([S:36]([CH3:39])(=[O:38])=[O:37])=[CH:32][CH:31]=5)[N:23]4[N:22]=3)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[F:40][C:41]([F:46])([F:45])[C:42]([OH:44])=[O:43].C(Cl)Cl>>[F:40][C:41]([F:46])([F:45])[C:42]([OH:44])=[O:43].[CH3:39][S:36]([C:33]1[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[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]5)=[CH:15][CH:16]=4)=[N:22]3)=[CH:27][CH:28]=2)=[CH:31][CH:32]=1)(=[O:37])=[O:38]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 86661704HCID 86661704, compound

Product 1

HCID 86661703HCID 86661703, compoundYield 10%

Procedure

To a round bottom flask 4-{4-[7-(4-Methanesulfonyl-phenyl)-pyrrolo[2,1-f][1,2,4]-triazin-2ylamino)-phenyl}-piperidine-1-carboxylic acid tert butyl ester (7-% pure, 0.762 g, 0.00135 mol) and 3.0 M Trifluoroacetic acid in DCM (10 mL, 0.030 mol) were added. The mixture was stirred at room temperature for 1 h then the solvent was removed by rotary evaporation. The crude product was purified via HPLC reverse phase chromatography with 0.1% TFA in Water and 0.1% TFA in ACN. The collected fractions were lyophilized to give [7-(4-Methanesulfonyl-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-(4-piperidin-4-yl-phenyl)-amine; compound with trifluoro-acetic acid as a yellow fluffy solid (0.06 g, 10%). LCMS (E/I+) 448.1 (M+H). NMR 1H (CDCl3/DSMO-d6)-9.97 (s, 1H), 9.50 (s, 1H), 8.41 (d, 2H, J=8.52 Hz), 8.20 (s, 1H), 8.02 (d, 2H, J=8.51 Hz), 7.67 (d, 2H, J=8.67 Hz), 7.20 (d, 2H, J=7.6 Hz), 7.11 (d, 1H, J=4.90 Hz), 6.88 (d, 1H, J=4.88 Hz), 3.54 (d, 2H, J=12.06 Hz), 3.14 (s, 3H), 3.02 (m, 3H), 2.59 (m, 2H), 2.05 (m, 4H).

Workup

  1. customthe solvent was removed by rotary evaporation
  2. customThe crude product was purified via HPLC reverse phase chromatography with 0.1% TFA in Water and 0.1% TFA in ACN

Sources & evidence

ORD record
ord-afabce67ac044c61aa786bd57ac613f9
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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