Trifluoroacetic acid → HCID 24947476, compound

HRID 1643316Notes

Reaction equation

HRID 1643316 reaction equation
C(O)(C(F)(F)F)=O.[C:8]([N:11]([CH2:40][CH2:41][N:42]([CH3:44])[CH3:43])[C:12]1[CH:39]=[CH:38][C:15]([C:16]([NH:18][C:19]2[CH:24]=[C:23]([C:25]3[S:26][CH:27]=[CH:28][CH:29]=3)[CH:22]=[CH:21][C:20]=2[NH:30]C(=O)OC(C)(C)C)=[O:17])=[CH:14][CH:13]=1)(=[O:10])[CH3:9]>C(Cl)Cl>[C:8]([N:11]([CH2:40][CH2:41][N:42]([CH3:43])[CH3:44])[C:12]1[CH:39]=[CH:38][C:15]([C:16]([NH:18][C:19]2[CH:24]=[C:23]([C:25]3[S:26][CH:27]=[CH:28][CH:29]=3)[CH:22]=[CH:21][C:20]=2[NH2:30])=[O:17])=[CH:14][CH:13]=1)(=[O:10])[CH3:9]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86633810HCID 86633810, compound

Product 1

HCID 24947476HCID 24947476, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (0.5 mL) was added to the tert-butyl [2-[(4-{acetyl[2-(dimethylamino)ethyl]amino}benzoyl)amino]-4-(2-thienyl)phenyl]carbamate (0.05 g, 0.096 mmol) in DCM (1 mL). The reaction mixture was stirred for 45 min. LC/MS shows mass for the product. The mixture was concentrated and 1H NMR was taken to show pure compound. 1H NMR (600 MHz, MeOH-d4) δ 8.20 (d, J=8.4 Hz, 2H), 8.69 (d, J=1.8 Hz, 1H), 7.65 (dd, J=2.0, 8.4 Hz, 1H), 7.57 (d, J=8.4 Hz, 2H), 7.43 (dd, J=4.3, 7.4 Hz, 2H), 7.38 (d, J=8.4 Hz, 1H), 7.11 (dd, J=3.7, 5.1 Hz, 1H), 4.13 (t, J=6.1 Hz, 2H), 3.31-3.34 (m, 2H), 3.00 (s, 6H), 1.92 (s. 3H); MS: cal'd 423 (MH+), exp 423 (MH+).

Workup

  1. concentrationThe mixture was concentrated

Sources & evidence

ORD record
ord-03d0ce7443cc49d784eab9f6b8da3eec
Source dataset
uspto-grants-2012_02
Patent number
US08119685B2

Reaction notes

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