Ammonium Hydroxide → HCID 86662382, compound

HRID 578636Notes

Reaction equation

HRID 578636 reaction equation
CO[C:3]([C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:14]=1[N:13]=[CH:12][N:11]=[C:10]2[NH:15][C@@H:16]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:17][N:18]=[N+:19]=[N-:20])=[O:4].[OH-].[NH4+:28]>C(O)(C)C.C1COCC1.O>[N:18]([CH2:17][C@@H:16]([NH:15][C:10]1[C:9]2[C:14](=[C:5]([C:3]([NH2:28])=[O:4])[CH:6]=[CH:7][CH:8]=2)[N:13]=[CH:12][N:11]=1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)=[N+:19]=[N-:20]

Participants

6

Reactant 2

HCID 14923Ammonium HydroxideHCID 86662383HCID 86662383, compound

Product 1

HCID 86662382HCID 86662382, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3776IsopropanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-((S)-2-Azido-1-phenyl-ethylamino)-quinazoline-8-carboxylic acid methyl ester (0.5 g, 1.48 mmol) in isopropanol (0.5 mL) and THF (0.5 mL) was added ammonium hydroxide (28-30% solution, 7.5 mL). The reaction was stirred for 24 hours then diluted with water. Solid formed collected by filtration and dried under vacuum (0.28 g, 57%). 1H NMR (400 MHz, DMSO-d6) δ ppm 3.72-3.81 (m, 1 H) 3.91 (dd, J=12.57, 9.98 Hz, 1 H) 5.73-5.85 (m, 1 H) 7.25-7.32 (m, 1 H) 7.36 (t, J=7.47 Hz, 2 H) 7.52 (d, J=7.27 Hz, 2 H) 7.71 (t, J=7.86 Hz, 1 H) 7.77-7.88 (m, 1 H) 8.60 (dd, J=7.47, 1.32 Hz, 1 H) 8.58 (s, 1 H) 8.66 (dd, J=8.32, 1.39 Hz, 1 H) 8.95 (d, J=8.30 Hz, 1 H) 10.26 (br. s., 1 H).

Workup

  1. customSolid formed
  2. filtrationcollected by filtration
  3. customdried under vacuum (0.28 g, 57%)

Sources & evidence

ORD record
ord-85d2f8538e11454598ca5c8f578aedfc
Source dataset
uspto-grants-2015_05
Patent number
US09040560B2

Reaction notes

Loading…