3-Amino-1,2-propanediol → HCID 22390592, compound

HRID 1071938Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6](OC2C=CC(Cl)=CC=2)[C:5]([C:16]#[N:17])=[CH:4][N:3]=1.[CH3:18][O:19][CH2:20][CH2:21][CH2:22][NH:23][S:24]([C:27]1[CH:33]=[CH:32][C:30]([NH2:31])=[CH:29][CH:28]=1)(=[O:26])=[O:25].[NH2:34][CH2:35][CH:36]([OH:39])[CH2:37][OH:38]>CC(O)CC>[C:16]([C:5]1[C:6]([NH:34][CH2:35][CH:36]([OH:39])[CH2:37][OH:38])=[N:7][C:2]([NH:31][C:30]2[CH:29]=[CH:28][C:27]([S:24](=[O:26])(=[O:25])[NH:23][CH2:22][CH2:21][CH2:20][O:19][CH3:18])=[CH:33][CH:32]=2)=[N:3][CH:4]=1)#[N:17]

Participants

Conditions

Temperature: 50 °C

Procedure

A suspension of 2-chloro-4-(4-chlorophenoxy)-5-cyanopyrimidine (Method 115; 179 mg, 0.68 mmol) and 4-[N-(3-methoxypropyl)sulphamoyl]aniline (Method 4; 149 mg, 0.61 mmol) in 2-butanol (6 ml) was heated and stirred at 50° C. for 5 hours. 3-Amino-1,2-propanediol (309 mg, 3.4 mmol) was then added and the temperature was raised to 90° C. and the reaction was stirred at this temperature for a further 18 hours. The solvent was removed by evaporation and the resulting solid was recrystallized from ethanol to give the title compound (104 mg, 39%). NMR: 1.55 (m, 2H), 2.75 (m, 2H), 3.15 (s, 3H), 3.25 (m, 2H), 3.40 (m, 3H), 3.60 (m, 1H), 3.75 (m, 1H), 4.70 (t, 1H), 5.85 (m, 1H), 7.35 (t, 1H), 7.55 (brs, 1H), 7.70 (d, 2H), 7.95 (d, 2H), 8.40 (s, 1H), 10.20 (s, 1H); m/z: 436.

Workup

temperaturewas heated
temperaturethe temperature was raised to 90° C.
stirringthe reaction was stirred at this temperature for a further 18 hours
customThe solvent was removed by evaporation
customthe resulting solid was recrystallized from ethanol

Sources & evidence

ORD record: ord-53e901e4d4424c4990eb41db47274fd3
Source dataset: uspto-grants-2005_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06908920B2

Reaction notes

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