Ammonia → HCID 135962806, compound

HRID 710919Notes

Reaction equation

HRID 710919 reaction equation
Cl.[CH:2]1([NH:8][C:9]2[NH:14][C:13](=[O:15])[CH:12]=[C:11]([C:16]3[C:24]4[C:19](=[N:20][CH:21]=[CH:22][CH:23]=4)[NH:18][CH:17]=3)[N:10]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.N>CO>[CH:2]1([NH:8][C:9]2[NH:14][C:13](=[O:15])[CH:12]=[C:11]([C:16]3[C:24]4[C:19](=[N:20][CH:21]=[CH:22][CH:23]=4)[NH:18][CH:17]=3)[N:10]=2)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 136341114HCID 136341114, compound

Product 1

HCID 135962806HCID 135962806, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

The HCl salt from EXAMPLE 1D was dissolved in methanol (500 mL) and 7M ammonia in methanol (13.9 mL, 97 mmol) was added dropwise. The mixture was stirred at room temperature for 10 minutes and concentrated. The residue was washed with water and concentrated to provide the title compound as the free base. MS (ESI) m/e 310 (M+H)+; 1H NMR (DMSO-d6) δ 1.17-1.81 (m, 8H), 1.93-2.07 (m, 2H), 3.71-3.98 (m, 1H), 6.05 (s, 1H), 6.37 (d, J=6.35 Hz, 1H), 7.15 (dd, J=8.13, 4.56 Hz, 1H), 8.19 (d, J=2.78 Hz, 1H), 8.25 (dd, J=4.76, 1.59 Hz, 1H), 8.63 (d, J=7.14 Hz, 1H), 10.17 (s, 1H), 12.11 (s, 1H).

Workup

  1. concentrationconcentrated
  2. washThe residue was washed with water
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-8267003924c64bab9376281eba7560b2
Source dataset
uspto-grants-2015_11
Patent number
US09181246B2

Reaction notes

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