Ammonia → HCID 24771685, compound

HRID 1429600Notes

Reaction equation

HRID 1429600 reaction equation
[CH:1]1([N:4]2[CH2:10][CH2:9][CH2:8][N:7]([C:11]([C:13]3[N:18]=[C:17]([C:19]#[N:20])[C:16]([O:21][C:22]4[CH:27]=[CH:26][C:25]([S:28][CH3:29])=[CH:24][CH:23]=4)=[CH:15][CH:14]=3)=[O:12])[CH2:6][CH2:5]2)[CH2:3][CH2:2]1.N.[OH:31]O>CO.C(Cl)Cl>[CH:1]1([N:4]2[CH2:10][CH2:9][CH2:8][N:7]([C:11]([C:13]3[N:18]=[C:17]([C:19]([NH2:20])=[O:31])[C:16]([O:21][C:22]4[CH:23]=[CH:24][C:25]([S:28][CH3:29])=[CH:26][CH:27]=4)=[CH:15][CH:14]=3)=[O:12])[CH2:6][CH2:5]2)[CH2:2][CH2:3]1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 784Hydrogen PeroxideHCID 24771632HCID 24771632, compound

Product 1

HCID 24771685HCID 24771685, compoundYield 26%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 6-(4-cyclopropyl-[1,4]diazepane-1-carbonyl)-3-(4-methylsulfanyl-phenoxy)-pyridine-2-carbonitrile (171.0 mg), 28% aq. NH3 (5 mL), and 30% aq. H2O2 (1.0 mL) in MeOH (4.0 mL) was stirred for 1.5 h. The mixture was diluted with DCM and washed with satd. aq. Na2S2O3. The organic layer was dried and concentrated. The residue was purified by reverse-phase HPLC followed by FCC to give the title compound (46.4 mg, 26%). MS (ESI): mass calcd. for C22H26N4O3S, 426.17; m/z found, 427.8 [M+H]+. 1H NMR (d6-acetone): 7.74-7.72 (dd, J=8.5, 2.5 Hz, 1H), 7.55 (br s, 1H), 7.51-7.49 (dd, J=8.5, 1.5 Hz, 1H), 7.33 (d, J=8.5 Hz, 2H), 7.03 (d, J=8.5 Hz, 2H), 6.82 (br s, 1H), 3.71-3.68 (m, 2H), 3.65-3.61 (m, 2H), 2.93-2.88 (m, 2H), 2.85-2.80 (m, 2H), 2.49 (s, 3H), 1.96-1.80 (m, 3H), 0.46-0.44 (m, 1H), 0.42-0.40 (m, 1H), 0.37-0.36 (m, 1H), 0.32-0.30 (m, 1H).

Workup

  1. washwashed with satd
  2. customThe organic layer was dried
  3. concentrationconcentrated
  4. customThe residue was purified by reverse-phase HPLC

Sources & evidence

ORD record
ord-c332e9e7d4f04924a3e9c16f4183f2f9
Source dataset
uspto-grants-2015_01
Patent number
US08940731B2

Reaction notes

Loading…