Ammonium Hydroxide → HCID 611101, compound

HRID 1110103Notes

Reaction equation

HRID 1110103 reaction equation
Cl.Cl.Cl[CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][N:9]([CH2:12][C:13]([N:15]2[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=3[C:19](=[O:26])[NH:18][C:17]3[CH:27]=[CH:28][CH:29]=[N:30][C:16]2=3)=[O:14])[CH2:8][CH2:7]1.[NH4+:31].[OH-]>>[NH2:31][CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][N:9]([CH2:12][C:13]([N:15]2[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=3[C:19](=[O:26])[NH:18][C:17]3[CH:27]=[CH:28][CH:29]=[N:30][C:16]2=3)=[O:14])[CH2:8][CH2:7]1

Participants

3

Reactant 2

HCID 14923Ammonium HydroxideHCID 19019105HCID 19019105, compound

Product 1

HCID 611101HCID 611101, compoundYield 97%

Procedure

Compound 26 (8.6 mg,0.017 mmol) was dissolved in concentrated NH4OH (0.4 mL) and stirred overnight. The crude product was extracted into CHCl3, and the organic layer was evaporated to dryness. The remaining residue was recrystallized from chloroform/petroleum ether to yield 7.2 mg of 27 (97%); mp 188°-190 ° C.: 1H NMR (CDCl3) δ 2.00-2.70 (m, 12 H), 3.20 (d, J=14 Hz, 1 H), 3.60 (br d, J=14 Hz, 1 H), 7.26 (dd, J= 7.8, 4.7 Hz, 1 H), 7.40 (m, 1 H), 7.55 (dd, J= 7.9, 1.4 Hz, 1 H), 7.58-7.62 (br s, 1 H), 7.92 (d, J= 7.7 Hz, 1 H), 8.26 (br s, 1 H), 9.35 (br s, 1 H); MS (CI/NH3) m/e 381 (MH+base) , 338, 252, 212.

Workup

  1. extractionThe crude product was extracted into CHCl3
  2. customthe organic layer was evaporated to dryness
  3. customThe remaining residue was recrystallized from chloroform/petroleum ether

Sources & evidence

ORD record
ord-b44c5a8007914a24aaa80fd5b462cfb8
Source dataset
uspto-grants-1994_06
Patent number
US05324832

Reaction notes

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