Dichloromethane → HCID 66712091, compound

HRID 1262294Notes

Reaction equation

HRID 1262294 reaction equation
C([O:5][C:6](=[O:38])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[N:23]2[C:18]([CH:19]=[N:20][C:21]([NH:24][C:25]3[CH:30]=[CH:29][C:28]([N:31]4[CH2:36][CH2:35][N:34]([CH3:37])[CH2:33][CH2:32]4)=[CH:27][CH:26]=3)=[N:22]2)=[CH:17][CH:16]=1)(C)(C)C.C(Cl)Cl.FC(F)(F)C(O)=O>>[CH3:37][N:34]1[CH2:35][CH2:36][N:31]([C:28]2[CH:27]=[CH:26][C:25]([NH:24][C:21]3[N:20]=[CH:19][C:18]4=[CH:17][CH:16]=[C:15]([C:10]5[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=5[O:8][CH2:7][C:6]([OH:38])=[O:5])[N:23]4[N:22]=3)=[CH:30][CH:29]=2)[CH2:32][CH2:33]1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 66711361HCID 66711361, compound

Product 1

HCID 66712091HCID 66712091, compoundYield 20%

Procedure

Into an 8-dram vial, (2-{2-[4-(4-Methyl-piperazin-1-yl)-phenylamino]-pyrrolo[2,1-f][1,2,4]triazin-7-yl}-phenoxy)-acetic acid tert-butyl ester (0.180 g, 0.350 mmol), Methylene chloride (5.0 mL, 78 mmol), and Trifluoroacetic Acid (1.00 mL, 13.0 mmol) were added. The reaction was stirred at room temperature overnight. The reaction was partitioned with saturated NaHCO3 and DCM. The organic was separated, washed with Brine and dried over Na2SO4. The solid was filtered and washed with DCM. The solvent was removed under vacuum. The reaction mixture 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 (2-{2-[4-(4-Methyl-piperazin-1-yl)-phenylamino]-pyrrolo[2,1-f][1,2,4]triazin-7-yl}-phenoxy)-acetic acid as a yellow solid (32 mg, 20%). LCMS (E/I+) 459.14 (M+H). NMR 1H (DMSO-d6)-13.28 (bs, 1H), 9.58 9 bs, 1H), 9.24 (s, 1H), 8.92 (s, 1H), 8.07 (d, 1H, J=7.44 Hz), 7.65 (d, 2H, J=8.12 Hz), 7.40 (t, 1H, J=8.12 Hz), 7.17-7.20 (m , 2H), 7.10 9 d, 1H, J=8.79 Hz), 6.85-6.93 (m, 3H), 4.75 (s, 2H), 3.74 (d, 2H, J=12.85 Hz), 3.53 (d, 2H, J=11.50 Hz), 3.18 (q, 2H, J=10.15 Hz), 2.80-2.93 (m, 5H).

Workup

  1. customThe reaction was partitioned with saturated NaHCO3 and DCM
  2. customThe organic was separated
  3. washwashed with Brine
  4. dry with materialdried over Na2SO4
  5. filtrationThe solid was filtered
  6. washwashed with DCM
  7. customThe solvent was removed under vacuum
  8. customThe reaction mixture was purified via HPLC

Sources & evidence

ORD record
ord-3f37f78e6ea542aa8318719e31a3a52f
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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