Trifluoroacetic acid → (E)-N-(2-Amino-phenyl)-3-{4-[1-(4-chloro-phenylcarbamoyl)-2-(3-diethylamino-pyrrolidin-1-yl)-ethyl]phenyl}-acrylamide

HRID 220195Notes

Reaction equation

HRID 220195 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][C:15](=[O:46])/[CH:16]=[CH:17]/[C:18]1[CH:23]=[CH:22][C:21]([CH:24]([C:36](=[O:45])[NH:37][C:38]2[CH:43]=[CH:42][C:41]([Cl:44])=[CH:40][CH:39]=2)[CH2:25][N:26]2[CH2:30][CH2:29][CH:28]([N:31]([CH2:34][CH3:35])[CH2:32][CH3:33])[CH2:27]2)=[CH:20][CH:19]=1)(C)(C)C.C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[NH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][C:15](=[O:46])/[CH:16]=[CH:17]/[C:18]1[CH:19]=[CH:20][C:21]([CH:24]([C:36](=[O:45])[NH:37][C:38]2[CH:43]=[CH:42][C:41]([Cl:44])=[CH:40][CH:39]=2)[CH2:25][N:26]2[CH2:30][CH2:29][CH:28]([N:31]([CH2:34][CH3:35])[CH2:32][CH3:33])[CH2:27]2)=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 59238288(E)-[2-(3-{4-[1-(4-Chloro-phenylcarbamoyl)-2-(3-diethylamino-pyrrolidin-1-yl)-ethyl]-phenyl}-acryloylamino)-phenyl]-carbamic acid tert-butyl ester

Product 1

HCID 59238301(E)-N-(2-Amino-phenyl)-3-{4-[1-(4-chloro-phenylcarbamoyl)-2-(3-diethylamino-pyrrolidin-1-yl)-ethyl]phenyl}-acrylamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (E)-[2-(3-{4-[1-(4-chloro-phenylcarbamoyl)-2-(3-diethylamino-pyrrolidin-1-yl)-ethyl]-phenyl}-acryloylamino)-phenyl]-carbamic acid tert-butyl ester (528 mg, 0.8 mmol) in CH2Cl2 (10 mL) was added CF3COOH (612 uL, 8 mmol). The mixture was stirred for about 4 h, and then NaHCO3 was added to the reaction system. After filtration of solids, the crude mixture was purified by preparative HPLC to obtain a light yellow solid. MS: calc'd 560 (MH+), exp 560 (MH+). 1H NMR (d4-MeOD, 400 MHz), 7.66 (d, 1H, J=15.6 Hz), 7.60-7.57 (m, 4H), 7.49 (d, 2H, J=8.0 Hz), 7.29 (d, 2H, J=8.8 Hz), 7.22 (d, 1H, J=7.6 Hz), 7.06 (t, 1H, J=7.6 Hz), 6.89 (d, 1H, J=8.8 Hz), 6.84 (d, 1H, J=15.6 Hz), 6.76 (t, 1H, J=7.6 Hz), 3.94 (m, 1H), 3.48-3.35 (m, 2H), 2.82-2.53 (broad m, 9H), 2.01-1.95 (m, 1H), 1.74-1.71 (m, 1H), 1.00 (q, 6H, J=7.0 Hz).

Workup

  1. filtrationAfter filtration of solids
  2. customthe crude mixture was purified by preparative HPLC
  3. customto obtain a light yellow solid

Sources & evidence

ORD record
ord-adc3bfdbb43d4cb4890e50c041d95b24
Source dataset
uspto-grants-2012_06
Patent number
US08202866B2

Reaction notes

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