Methanesulfonic Acid → HCID 89845238, Verbindung

HRID 539904Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 539904
[Cl:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([NH:11][C:12]3[N:17]=[C:16]([N:18]4[CH:22]=[C:21]([CH2:23][N:24]5[CH2:27][CH:26]([OH:28])[CH2:25]5)[C:20]([CH3:29])=[N:19]4)[CH:15]=[CH:14][N:13]=3)[CH:9]=2)[N:4]([CH3:30])[CH:3]=1.[CH3:31][S:32](O)(=[O:34])=[O:33]>CO>[CH3:31][S:32]([O:28][CH:26]1[CH2:25][N:24]([CH2:23][C:21]2[C:20]([CH3:29])=[N:19][N:18]([C:16]3[CH:15]=[CH:14][N:13]=[C:12]([NH:11][C:8]4[CH:9]=[C:10]5[C:5](=[CH:6][CH:7]=4)[N:4]([CH3:30])[CH:3]=[C:2]5[Cl:1])[N:17]=3)[CH:22]=2)[CH2:27]1)(=[O:34])=[O:33]

Komponenten

4

Edukt 2

HCID 6395Methanesulfonic AcidHCID 71698378HCID 71698378, Verbindung2×

Produkt 1

HCID 89845238HCID 89845238, VerbindungAusbeute 54 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a slurry of 1-((1-(2-(3-chloro-1-methyl-1H-indol-5-ylamino)pyrimidin-4-yl)-3-methyl-1H-pyrazol-4-yl)methyl)azetidin-3-ol, Compound No. 144 (127 mg, 0.3 mmol) in methanol, was added 1 equivalant of methanesulfonic acid at room temperature. After being stirred at room temperature, the resulting solids were collected by filtration, rinsed with cold methanol and then vacuum dried to give 85 mg (54%) of the desired compound 181 as a pale yellow solid. MS (ESI) m/z 424 [M+H]+; 1H NMR (300 MHz, DMSO-d6) δ 9.9 (br s, 1H), 9.98 (s, 1H), 8.66 (s, 1H), 8.53 (d, 1H, J=5.4 Hz), 7.92 (S, 1H), 7.53˜7.51 (m, 3H), 7.19 (d, 1H, J=5.4 Hz), 4.45˜4.50 (m, 1H), 4.32˜4.38 (m, 2H), 4.22˜4.28 (m, 2H), 3.85˜3.91 (m, 2H), 3.79 (s, 3H), 2.36 (s, 3H).

Aufarbeitung

  1. filtrationthe resulting solids were collected by filtration
  2. washrinsed with cold methanol
  3. customvacuum dried

Quellen und Nachweise

ORD-Eintrag
ord-2aaad86033d04845a51a416e36ab8013
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08871778B2

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