Ammonia → HCID 24771685, compound

HRID 631898Notes

Reaction equation

HRID 631898 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-090577a04d01423f93237ce23857cb8d
Source dataset
uspto-grants-2016_04
Patent number
US09321729B2

Reaction notes

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