Trifluoroacetic acid → Trifluoroacetic acid

HRID 2410925Notes

Reaction equation

HRID 2410925 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([C:30]2[CH:35]=[CH:34][C:33]([CH2:36][N:37]3[CH2:42][CH2:41][O:40][CH2:39][CH2:38]3)=[C:32]([CH3:43])[CH:31]=2)[CH:7]=[C:8]2[C:16]=1[NH:15][C:14]1[CH:13]=[C:12]([C:17]3[CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][CH:18]=3)[CH:11]=[CH:10][C:9]2=1)(=[O:3])[NH2:2].[C:44]([OH:50])([C:46]([F:49])([F:48])[F:47])=[O:45]>ClCCCl>[CH3:43][C:32]1[CH:31]=[C:30]([C:6]2[CH:5]=[C:4]([C:1]([NH2:2])=[O:3])[C:16]3[NH:15][C:14]4[C:9]([C:8]=3[CH:7]=2)=[CH:10][CH:11]=[C:12]([C:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH:18]=2)[CH:13]=4)[CH:35]=[CH:34][C:33]=1[CH2:36][N:37]1[CH2:42][CH2:41][O:40][CH2:39][CH2:38]1.[C:44]([OH:50])([C:46]([F:49])([F:48])[F:47])=[O:45]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66615383HCID 66615383, compound

Product 2

HCID 6422Trifluoroacetic acidHCID 66604590HCID 66604590, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

tert-Butyl 4-(8-carbamoyl-6-(3-methyl-4-(morpholinomethyl)phenyl)-9H-carbazol-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate 484 (3 mg, 5.17 μmol) was mixed with TFA (0.2 mL, 2.60 mmol) in 1,2-Dichloroethane (0.4 mL). The mixture was stirred at r.t. for 1 hr. The mixture was concentrated to give the titled product as TFA salt. MS (ESI) m/z 481.07 (M+H)+. 1H NMR (MeOD-d4) δ ppm 8.60 (d, 1H, J=1.8), 8.27 (d, 1H, J=1.8), 8.21 (d, 1H, J=8.2), 7.87 (s, 1H), 7.82 (dd, 1H, J=7.9, 1.5), 7.75 (d, 1H, J=1.3), 7.63 (d, 1H, J=7.9), 7.43 (dd, 1H, J=8.2, 1.5), 6.31 (bs, 1H), 4.51 (s, 2H), 4.1-3.85 (m, 6H), 3.56 (t, 2H, J=6.1), 3.47-3.2 (m, 4H), 2.98 (bs, 2H), 2.63 (s, 3H).

Workup

  1. concentrationThe mixture was concentrated

Sources & evidence

ORD record
ord-13705ed070364d8b8933bd5e4a6dd442
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

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