Trifluoroacetic acid → HCID 178492377, compound

HRID 2117264Notes

Reaction equation

HRID 2117264 reaction equation
[O:1]=[C:2]1[C:8](=[CH:9][C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:12](C(OC(C)(C)C)=O)[N:11]=2)[C:7](=[O:26])[N:6]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:5]=[CH:4][N:3]1[CH2:33][C:34]([N:36]([CH:45]([CH3:47])[CH3:46])[C:37]1[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[CH:39][CH:38]=1)=[O:35].C(O)(C(F)(F)F)=O>C(Cl)(Cl)Cl>[O:1]=[C:2]1[C:8](=[CH:9][C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[NH:12][N:11]=2)[C:7](=[O:26])[N:6]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:5]=[CH:4][N:3]1[CH2:33][C:34]([N:36]([CH:45]([CH3:47])[CH3:46])[C:37]1[CH:38]=[CH:39][C:40]([O:43][CH3:44])=[CH:41][CH:42]=1)=[O:35]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69224763HCID 69224763, compound

Product 1

HCID 178492377HCID 178492377, compoundYield 94.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The 2-[2,4-dioxo-3-(1-tert-butyloxycarbonyl-1H-indazol-3-ylmethylene)-5-phenyl-2,3,4,5-tetrahydro-1H-1,5-diazepin-1-yl]-N-isopropyl-N-(4-methoxyphenyl)acetamide (170 mg) was dissolved in CHCl3 (10 ml) and TFA (5 ml) was added. The reaction mixture was stirred for 6 hrs and the solvents were removed in vacuo. The crude product was purified by RP HPLC Dynamax (C-8) (10 ml/min (50% Acetonitrile, 50% Water (0.1% TFA), followed by lyophilization, to afford the titled product of Example 1 (135 mg) as a white lyophilate. HPLC Column: Dynamax C-8 2 ml/min., 30-70% Acetonitrile in aqueous TFA (0.1% v/v) over 20 min., Tr=17.1 min. 1H NMR (400 MHz, CDCl3) 7.93 (d, J=8.3 Hz, 1H), 7.59 (m, 2H), 7.11 (m, 2H), 7.31 (m, 6H), 6.93 (m, 2H), 6.00 (s, 2H), 4.92 (sept., J=6.3 Hz, 1H), 4.15 (m, 1H), 3.92 (m, 4H), 3.82 (s, 3H), 1.04 (d, J=6.3 Hz, 6H), MS (FAB) [M+H]+=538.

Workup

  1. customthe solvents were removed in vacuo
  2. customThe crude product was purified by RP HPLC Dynamax (C-8) (10 ml/min (50% Acetonitrile, 50% Water (0.1% TFA)

Sources & evidence

ORD record
ord-faf59b53872b44b18395d16acd1739ea
Source dataset
uspto-grants-2008_10
Patent number
US07442693B2

Reaction notes

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