Ammonium Hydroxide → HCID 71205425, compound

HRID 2280860Notes

Reaction equation

HRID 2280860 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]2[C:11]([C:18]3[C:23]([Cl:24])=[CH:22][CH:21]=[CH:20][C:19]=3[Cl:25])=[N:12][O:13][C:14]=2[CH:15]2[CH2:17][CH2:16]2)[CH:5]=[CH:4][C:3]=1[C:26]1([OH:40])[CH2:29][CH:28]([C:30]2[CH:31]=[C:32]([S:36](Cl)(=[O:38])=[O:37])[CH:33]=[CH:34][CH:35]=2)[CH2:27]1.[NH4+:41].[OH-]>CC#N>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]2[C:11]([C:18]3[C:23]([Cl:24])=[CH:22][CH:21]=[CH:20][C:19]=3[Cl:25])=[N:12][O:13][C:14]=2[CH:15]2[CH2:17][CH2:16]2)[CH:5]=[CH:4][C:3]=1[C:26]1([OH:40])[CH2:29][CH:28]([C:30]2[CH:31]=[C:32]([S:36]([NH2:41])(=[O:38])=[O:37])[CH:33]=[CH:34][CH:35]=2)[CH2:27]1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 89375931HCID 89375931, compound

Product 1

HCID 71205425HCID 71205425, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To the solution of compound 5b (30 mg) in CH3CN (2 mL) was added NH4OH (0.3 mL). The mixture was stirred at rt for 1 h. Concentration to dryness and purification by prep. RP-HPLC gave the title compound 5 (3.5 mg, 10% for two steps) as a white solid. 1H NMR (400 MHz, CDCl3) δ: 7.85 (s, 1H), 7.77 (d, J=7.6 Hz, 1H), 7.54-7.41 (m, 5H), 7.35 (d, J=8.4 Hz, 1H), 6.90 (s, 1H), 6.75 (d, J=8.4 Hz, 1H), 4.83 (s, 2H), 4.77 (s, broad, 2H), 3.20 (t, J=10.4 Hz, 2H), 3.04 (m, 1H), 2.58 (t, J=10.6 Hz, 2H), 2.17 (m, 1H), 1.31-1.30 (m, 2H), 1.20-1.16 (m, 2H). MS (ESI−) m/z: 617 [M−1]−.

Workup

  1. concentrationConcentration
  2. customto dryness and purification by prep

Sources & evidence

ORD record
ord-561ba73b2be443e6928a99994941493e
Source dataset
uspto-grants-2015_09
Patent number
US09139539B2

Reaction notes

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