Trifluoroacetic acid → Trifluoroacetic acid

HRID 1093153Notes

Reaction equation

HRID 1093153 reaction equation
C([O:8][C:9]1[C:21](=[O:22])[N:13]2[CH2:14][CH:15]3[CH2:20][CH2:19][N:18]([C:12]2=[N:11][C:10]=1[C:23]([NH:25][CH2:26][C:27]1[CH:32]=[CH:31][C:30]([F:33])=[CH:29][C:28]=1[N:34]1[CH2:38][C:37]([CH3:40])([CH3:39])[N:36]([CH3:41])[S:35]1(=[O:43])=[O:42])=[O:24])[CH2:17][CH2:16]3)C1C=CC=CC=1.[F:44][C:45]([F:50])([F:49])[C:46]([OH:48])=[O:47]>C(Cl)Cl>[F:33][C:30]1[CH:31]=[CH:32][C:27]([CH2:26][NH:25][C:23]([C:10]2[N:11]=[C:12]3[N:18]4[CH2:17][CH2:16][CH:15]([CH2:20][CH2:19]4)[CH2:14][N:13]3[C:21](=[O:22])[C:9]=2[OH:8])=[O:24])=[C:28]([N:34]2[CH2:38][C:37]([CH3:40])([CH3:39])[N:36]([CH3:41])[S:35]2(=[O:43])=[O:42])[CH:29]=1.[F:44][C:45]([F:50])([F:49])[C:46]([OH:48])=[O:47]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 579052343-(Benzyloxy)-N-(4-fluoro-2-(4,4,5-trimethyl-1,1-dioxido-1,2,5-thiadiazolidin-2-yl)benzyl)-4-oxo-6,7,8,9-tetrahydro-4H-7,10-ethanopyrimido[1,2-a][1,3]diazepine-2-carboxamide

Product 2

HCID 6422Trifluoroacetic acidHCID 57905039N-(4-Fluoro-2-(4,4,5-trimethyl-1,1-dioxido-1,2,5-thiadiazolidin-2-yl)benzyl)-3-hydroxy-4-oxo-6,7,8,9-tetrahydro-4H-7,10-ethanopyrimido[1,2-a][1,3]diazepine-2-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-(benzyloxy)-N-(4-fluoro-2-(4,4,5-trimethyl-1,1-dioxido-1,2,5-thiadiazolidin-2-yl)benzyl)-4-oxo-6,7,8,9-tetrahydro-4H-7,10-ethanopyrimido[1,2-a][1,3]diazepine-2-carboxamide (0.054 g, 0.088 mmol) in CH2Cl2 (5 mL) and trifluoroacetic acid (0.7 mL, 9.09 mmol) was stirred at room temperature for 18 h. The solution was concentrated to give a yellow oil that was purified by preparative HPLC (Solvent A=10% methanol/90% H2O/0.1% trifluoroacetic acid; Solvent B=90% methanol/10% H2O/0-1% trifluoroacetic acid; Start % B=20; Final % B=100; Gradient time=20 min; Stop time=25 min; Column=Sunfire 19×100 mm, C18, 5 μm) to give the title compound (as a trifluoroacetic acid salt) as a pale yellow solid (0.0075 g, 13% yield). LCMS (M+H) calcd for C23H30FN6O5S: 521.19; found: 521.25. 1H NMR (500 MHz, CDCl3) δ: 8.64 (1H, t, J=5.6 Hz), 7.60 (1H, dd, J=8.2, 6.4 Hz), 7.22 (1H, dd, J=9.2, 2.4 Hz), 7.11 (1H, td, J=8.1, 2.2 Hz), 4.64 (2H, d, J=5.8 Hz), 4.00-3.94 (2H, m), 3.79-3.76 (2H, m), 3.72 (2H, s), 3.58 (2H, s), 3.03 (1H, brs), 2.73 (3H, s), 2.32-2.28 (2H, m), 1.91-1.87 (2H, m), 1.46 (6H, s).

Workup

  1. concentrationThe solution was concentrated
  2. customto give a yellow oil that
  3. customwas purified by preparative HPLC (Solvent A=10% methanol/90% H2O/0.1% trifluoroacetic acid
  4. customGradient time=20 min
  5. customtime=25 min

Sources & evidence

ORD record
ord-ac267b6632914801ba2444fbb360c218
Source dataset
uspto-grants-2012_03
Patent number
US08129398B2

Reaction notes

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