Hydrochloric Acid → HCID 18463943, compound

HRID 2231080Notes

Reaction equation

HRID 2231080 reaction equation
[CH2:1]([N:8]1[C:14](=[O:15])[CH2:13][CH2:12][CH:11]([NH:16][C:17]([C:19]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:22]=[CH:21][N:20]=2)=[O:18])[C:10](=[O:29])[N:9]1[CH2:30][C:31](=[O:47])[NH:32][CH:33]1[CH2:37][C:36](=[O:38])[O:35][CH:34]1[O:39]CC1C=CC=CC=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.C(#N)C>O>[CH2:1]([N:8]1[C:14](=[O:15])[CH2:13][CH2:12][CH:11]([NH:16][C:17]([C:19]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:22]=[CH:21][N:20]=2)=[O:18])[C:10](=[O:29])[N:9]1[CH2:30][C:31]([NH:32][CH:33]([CH:34]=[O:39])[CH2:37][C:36]([OH:38])=[O:35])=[O:47])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6342AcetonitrileHCID 22956504HCID 22956504, compound

Product 1

HCID 18463943HCID 18463943, compoundYield 83.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Isoquinoline-1-carboxylic acid {1-benzyl-2-[(2-benzyloxy-5-oxo-tetrahydro-furan-3-ylcarbamoyl)-methyl]-3,7-dioxo-[1,2]diazepan-4-yl}-amide (10a, diastereomers) (14 mg, 0.022 mmol) was stirred in the solution of 10% HCl (1.5 mL) and acetonitrile (1 mL) for 4 hours. The reaction mixture was diluted with water (30 mL), washed with ether (30 mL) twice. The aqueous solution was purged with nitrogen for 30 min then cooled in dry ice and lyophilized overnight to afford 10 mg (83% yield) of the title compound. 1H-NMR (500 MHz, CD3OD) δ 2.00-2.10 (m, 1H), 2.32-2.50 (m, 2H), 3.62-3.72 (m, 1H), 4.15-4.35 (m, 2H), 4.45-4.80 (m, 4H), 5.25-5.32 (m, 1H), 7.30-7.68 (m, 5H), 7.95-8.05 (m, 1H), 8.12-8.17 (m, 1H), 8.22-8.27 (m, 1H), 8.35-8.41 (d, 1H), 8.56 (s, 1H), 8.65-8.74 (d, 1H). Analytical HPLC: 9.40 min. LC-MS (ES+): m/e=546 (M+H+).

Workup

  1. washwashed with ether (30 mL) twice
  2. customThe aqueous solution was purged with nitrogen for 30 min
  3. temperaturethen cooled in dry ice

Sources & evidence

ORD record
ord-01e87dd8653e4cfa9d4db9258a5757f0
Source dataset
uspto-grants-2002_07
Patent number
US06426413B1

Reaction notes

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