Trifluoroacetic acid → HCID 23598709, compound

HRID 891202Notes

Reaction equation

HRID 891202 reaction equation
[CH2:1]([NH:8][CH2:9][C:10]1[CH2:16][N:15]([CH2:17][C:18](=[O:29])[NH:19][CH:20]2[CH2:24][C:23](=[O:25])[O:22][CH:21]2[O:26]CC)[C:14](=[O:30])[CH:13]([NH:31][C:32]([C:34]2[C:43]3[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=3)[CH:37]=[CH:36][N:35]=2)=[O:33])[CH2:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>CC#N.O>[CH2:1]([NH:8][CH2:9][C:10]1[CH2:16][N:15]([CH2:17][C:18](=[O:29])[NH:19][CH:20]2[CH2:24][C:23](=[O:25])[O:22][CH:21]2[OH:26])[C:14](=[O:30])[CH:13]([NH:31][C:32]([C:34]2[C:43]3[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=3)[CH:37]=[CH:36][N:35]=2)=[O:33])[CH2:12][CH:11]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 23598708HCID 23598708, compound

Product 1

HCID 23598709HCID 23598709, compoundYield 38%

Reagents, catalysts & solvents 1

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

Procedure

Isoquinoline-1-carboxylic acid {6-(benzylamino-methyl)-1-[(2-ethoxy-5-oxo-tetrahydro-furan-3-ylcarbamoyl)-methyl]-2-oxo-2,3,4,7-tetrahydro-1H-azepin-3-yl}-amide, 26, prepared herein above, is treated with TFA in CH3CN/H2O. The solution is then concentrated in vacuo and the resulting residue it purified by preparative reverse phase HPLC to afford 30 mg (38% yield) of the desired product. 1H NMR (CD3OD) δ 9.20–9.17 (d, J=8.7 Hz, 1H), 8.57–8.56 (d, J=5.7 Hz, 1H), 8.06–8.02 (m, 2H), 7.88–7.83 (d, d, d, J=8.1, 6.6, 0.9 Hz, 1H), 7.79–7.73 (d, d, d, J=6.9, 6.9, 0.9 Hz, 1H), 7.64–7.60 (m, 2H), 7.55–7.47 (m, 3H), 6.14 (bs, 1H), 5.56–5.50 (d, d, J=12.3, 3.9 Hz, 1H), 4.85–4.79 (d, d, J=16.2, 1.8 Hz, 1H), 4.66–4.62 (d, d, J=9.0, 3.6 Hz, 1H), 4.39–4.25 (m, 4H), 3.89–3.68 (m, 4H), 2.99–2.93 (m, 1H), 2.74–2.45 (m, 4H), MS 557 (M+H)+.

Workup

  1. concentrationThe solution is then concentrated in vacuo
  2. customthe resulting residue it purified by preparative reverse phase HPLC

Sources & evidence

ORD record
ord-9501eefcb1d7495d818a089bb3703f68
Source dataset
uspto-grants-2006_02
Patent number
US07001899B2

Reaction notes

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