Dichloromethane → HCID 86661662, compound

HRID 1261879Notes

Reaction equation

HRID 1261879 reaction equation
C([O:5][C:6](=[O:35])[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:21]3[C:16]([CH:17]=[N:18][C:19]([NH:22][C:23]4[CH:28]=[CH:27][C:26]([N:29]5[CH2:34][CH2:33][O:32][CH2:31][CH2:30]5)=[CH:25][CH:24]=4)=[N:20]3)=[CH:15][CH:14]=2)=[CH:9][CH:8]=1)(C)(C)C.C(Cl)Cl.[F:39][C:40]([F:45])([F:44])[C:41]([OH:43])=[O:42]>>[F:39][C:40]([F:45])([F:44])[C:41]([OH:43])=[O:42].[N:29]1([C:26]2[CH:27]=[CH:28][C:23]([NH:22][C:19]3[N:18]=[CH:17][C:16]4=[CH:15][CH:14]=[C:13]([C:10]5[CH:11]=[CH:12][C:7]([C:6]([OH:35])=[O:5])=[CH:8][CH:9]=5)[N:21]4[N:20]=3)=[CH:24][CH:25]=2)[CH2:30][CH2:31][O:32][CH2:33][CH2:34]1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 66711719HCID 66711719, compound

Product 1

HCID 86661662HCID 86661662, compound

Procedure

Into a 1-neck round-bottom flask, [A] 4-[2-(4-Morpholin-4-yl-phenylamino)-pyrrolo[2,1-f][1,2,4]triazin-7-yl]-benzoic acid tert-butyl ester (0.34 g, 0.72 mmol), Methylene chloride (10 mL, 200 mmol) and Trifluoroacetic Acid (5.0 mL, 65 mmol) were added and stirred at room temperature overnight. The solvent was removed under vacuum. The resulting solid was washed with DCM to give 4-[2-(4-Morpholin-4-yl-phenylamino)-pyrrolo[2,1-f][1,2,4]triazin-7-yl]-benzoic acid; compound with trifluoro-acetic acid as a yellow solid. LCMS (E/I+) 416.16 (M+H). NMR 1H (DSMO-d6)-9.45 (s, 1H), 9.01 (s, 1H), 8.35 (d, 2H, J=8.40 Hz), 8.07 (d, 2H, J=8.41 Hz), 7.88 (s, 1H), 7.71 (d, 1, J=8.80 Hz), 7.30 (d 1H, J=4.76 Hz), 7.17 (d, 2H, J=8.44 Hz), 6.98 (d, 1H, J=4.80 Hz), 3.83 (t, 4H, J=4.78 Hz), 3.24 (bs, 4H).

Workup

  1. customThe solvent was removed under vacuum
  2. washThe resulting solid was washed with DCM

Sources & evidence

ORD record
ord-8abfce1351984e2ea32c545cffd3144e
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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