Trifluoroacetic acid → HCID 23598707, compound

HRID 891210Notes

Reaction equation

HRID 891210 reaction equation
[C:1]1([S:7]([NH:10][CH2:11][C:12]2[CH2:18][N:17]([CH2:19][C:20](=[O:31])[NH:21][CH:22]3[CH2:26][C:25](=[O:27])[O:24][CH:23]3[O:28]CC)[C:16](=[O:32])[CH:15]([NH:33][C:34]([C:36]3[C:45]4[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=4)[CH:39]=[CH:38][N:37]=3)=[O:35])[CH2:14][CH:13]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.FC(F)(F)C(O)=O>CC#N.O>[C:1]1([S:7]([NH:10][CH2:11][C:12]2[CH2:18][N:17]([CH2:19][C:20](=[O:31])[NH:21][CH:22]3[CH2:26][C:25](=[O:27])[O:24][CH:23]3[OH:28])[C:16](=[O:32])[CH:15]([NH:33][C:34]([C:36]3[C:45]4[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=4)[CH:39]=[CH:38][N:37]=3)=[O:35])[CH2:14][CH:13]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 23598706HCID 23598706, compound

Product 1

HCID 23598707HCID 23598707, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

A solution of isoquinoline-1-carboxylic acid {6-(benzenesulfonylamino-methyl)-1-[(2-ethoxy-5-oxo-tetrahydro-furan-3-ylcarbamoyl)-methyl]-2-oxo-2,3,4,7-tetrahydro-1H-azepin-3-yl}-amide, 35, as prepared in the above example, in CH3CN/H2O is treated with excess trifluoroacetic acid. The solution is stirred several hours then purified by preparative reverse phase HPLC to afford 150 mg (65% yield) of the desired product. 1H NMR (CD3OD) δ 9.14–9.11 (d, J=8.7 Hz, 1H), 8.55–8.53 (d, J=5.4 Hz, 1H), 8.07–8.03 (m, 2H), 7.93–7.85 (m, 3H), 7.81–7.76 (m, 1H), 7.68–7.60 (m, 3H), 5.68 (bs, 1H), 5.49–5.43 (d, d, J=12.3, 3.9 Hz, 1H), 4.68–4.62 (m, 2H), 4.41–4.32 (m, 1H), 4.30–4.01 (m, 2H), 3.55–3.48 (m, 3H), 2.81–2.67 (m, 2H), 2.57–2.49 (d, d, d, J=16.2, 8.4, 1.2 Hz, 1H), 2.46–2.36 (d, d, J=15.0, 15.0 Hz, 1H); MS 608 (M+H).

Workup

  1. customthen purified by preparative reverse phase HPLC

Sources & evidence

ORD record
ord-ea8b4a8dcde8473187e60be43e00d0d5
Source dataset
uspto-grants-2006_02
Patent number
US07001899B2

Reaction notes

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