Trifluoroacetic acid → HCID 23598705, compound

HRID 891208Notes

Reaction equation

HRID 891208 reaction equation
[C:1]([NH:9][CH2:10][C:11]1[CH2:17][N:16]([CH2:18][C:19](=[O:30])[NH:20][CH:21]2[CH2:25][C:24](=[O:26])[O:23][CH:22]2[O:27]CC)[C:15](=[O:31])[CH:14]([NH:32][C:33]([C:35]2[C:44]3[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=3)[CH:38]=[CH:37][N:36]=2)=[O:34])[CH2:13][CH:12]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>CC#N.O>[C:1]([NH:9][CH2:10][C:11]1[CH2:17][N:16]([CH2:18][C:19](=[O:30])[NH:20][CH:21]2[CH2:25][C:24](=[O:26])[O:23][CH:22]2[OH:27])[C:15](=[O:31])[CH:14]([NH:32][C:33]([C:35]2[C:44]3[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=3)[CH:38]=[CH:37][N:36]=2)=[O:34])[CH2:13][CH:12]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 23598704HCID 23598704, compound

Product 1

HCID 23598705HCID 23598705, compoundYield 51%

Reagents, catalysts & solvents 1

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

Procedure

A solution of isoquinoline-1-carboxylic acid {6-(benzoylamino-methyl)-1-[(2-ethoxy-5-oxo-tetrahydro-furan-3-ylcarbamoyl)-methyl]-2-oxo-2,3,4,7,-tetrahydro-1H-azepin-3-yl}-amide, 32, 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 51 mg (51% yield) of the desired product. 1H NMR (CD3OD) δ 9.15–9.12 (d, J=8.4 Hz, 1H), 8.56–8.54 (d, J=5.7 Hz, 1H), 8.08–8.04 (m, 2H), 7.92–7.76 (m, 4H), 7.57–7.50 (m, 3H), 5.83 (bs, 1H), 5.61–5.56 (d, d, J=12.6, 3.9 Hz, 1H), 4.90–4.85 (d, J=17.4 Hz, 1H), 4.63–4.60 (m, 1H), 4.41–4.01 (m, 3H), 3.65–3.58 (d, d, J=17.4, 2.7 Hz, 1H), 2.91–2.85 (bd, J=18.9 Hz, 1H), 2.75–2.65 (m, 1H), 2.55–2.46 (m, 2H); MS 572 (M+H).

Workup

  1. customthen purified by preparative reverse phase HPLC

Sources & evidence

ORD record
ord-0a90cc97c3544c3ca786259329a1937a
Source dataset
uspto-grants-2006_02
Patent number
US07001899B2

Reaction notes

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