Ammonium Hydroxide → HCID 136168821, compound

HRID 2368988Notes

Reaction equation

HRID 2368988 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:12]=[C:11]([NH:13][CH2:14][CH2:15][C:16](O)=[O:17])[N:10]3[N:19]=[CH:20][C:21]([C:22]4[CH:23]=[N:24][C:25]5[C:30]([CH:31]=4)=[CH:29][CH:28]=[CH:27][CH:26]=5)=[C:9]3[N:8]=2)[CH2:3][CH2:2]1.[NH4+].[OH-]>>[O:1]1[CH2:2][CH2:3][N:4]([C:7]2[C:12]3[C:16](=[O:17])[CH2:15][CH2:14][NH:13][C:11]=3[N:10]3[N:19]=[CH:20][C:21]([C:22]4[CH:23]=[N:24][C:25]5[C:30]([CH:31]=4)=[CH:29][CH:28]=[CH:27][CH:26]=5)=[C:9]3[N:8]=2)[CH2:5][CH2:6]1

Participants

3

Reactant 2

HCID 14923Ammonium HydroxideHCID 66584647HCID 66584647, compound

Product 1

HCID 136168821HCID 136168821, compound

Conditions

Temperature
125 °C

Procedure

A mixture of 3-(5-morpholino-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-7-ylamino)propanoic acid (19.8 mg, 0.047 mmoL) and PPA was heated at 125° C. for 2 h. The reaction was cooled to 0° C. and the PH was adjusted to 8 by the addition of NH4OH. Extraction with 20% iPrOH/CH2Cl2 (×3), concentration of dried organic layer and purification by prep-LC afforded 5-morpholino-3-(quinolin-3-yl)-8,9-dihydropyrazolo[1,5-a]pyrido[3,2-e]pyrimidin-6(7H)-one. LCMS tR=2.79 Min (10 min run, UV254nm). Mass calculated for, M+ 400.1, observed LC/MS m/z 401.1 (M+H).

Workup

  1. temperatureThe reaction was cooled to 0° C.
  2. extractionExtraction
  3. customwith 20% iPrOH/CH2Cl2 (×3), concentration of dried organic layer and purification

Sources & evidence

ORD record
ord-cacad6adefba44afa5c3d3f410baca23
Source dataset
uspto-grants-2014_04
Patent number
US08703784B2

Reaction notes

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