Hydrochloric Acid → HCID 58300040, compound

HRID 876029Notes

Reaction equation

HRID 876029 reaction equation
[CH:1]1([N:6]2[C:10]3[N:11]=[C:12]([NH:15][C:16]4[N:21]=[N:20][C:19]([N:22]5[CH2:27][CH2:26][N:25]([CH2:28][C:29]([O:31]CC)=[O:30])[CH2:24][CH2:23]5)=[CH:18][CH:17]=4)[N:13]=[CH:14][C:9]=3[C:8]3[CH:34]=[CH:35][N:36]=[CH:37][C:7]2=3)[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl>>[CH:1]1([N:6]2[C:10]3[N:11]=[C:12]([NH:15][C:16]4[N:21]=[N:20][C:19]([N:22]5[CH2:27][CH2:26][N:25]([CH2:28][C:29]([OH:31])=[O:30])[CH2:24][CH2:23]5)=[CH:18][CH:17]=4)[N:13]=[CH:14][C:9]=3[C:8]3[CH:34]=[CH:35][N:36]=[CH:37][C:7]2=3)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 58299768HCID 58299768, compound

Product 1

HCID 58300040HCID 58300040, compound

Conditions

Temperature
90 °C

Procedure

A mixture of compound 344 and hydrochloric acid (1 N aqueous solution) (7 mL) was stirred at 90° C. for 17 h. After concentration, the residue was subjected to reverse phase preparative HPLC (acetonitrile/H2O containing 0.1% TFA each, 40 min from 10 to 30%). Lyophilization provided compound 346 (50 mg) as a yellow solid (TFA salt). 1H NMR (500 MHz, DMSO-d6) δ ppm 10.94 (1 H, br. s.), 9.55 (1 H, s), 9.33 (1 H, s), 8.65 (1 H, d, J=6.1 Hz), 8.53 (1 H, d, J=5.9 Hz), 8.23 (1 H, d, J=9.5 Hz), 7.60 (1 H, d, J=9.8 Hz), 5.34 (1 H, dq, J=8.9, 8.8 Hz), 4.16 (2 H, br. s.), 3.40 (8 H, br. s.), 2.33-2.44 (2 H, m), 1.92-2.18 (4 H, m), 1.62-1.81 (2 H, m). LCMS-ESI (POS), M/Z, M+1: Found 474.2.

Workup

  1. concentrationAfter concentration
  2. custom40 min

Sources & evidence

ORD record
ord-39f144389eee4689b759203419713886
Source dataset
uspto-grants-2015_03
Patent number
US08980903B2

Reaction notes

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