N-methyl-2-pyrrolidone → HCID 21919247, compound

HRID 1244327Notes

Reaction equation

HRID 1244327 reaction equation
Cl[C:2]1[N:7]=[C:6]2[NH:8][C:9]([C:11]3[S:12][C:13]4[C:19]([N:20]5[CH2:25][CH2:24][O:23][CH2:22][CH2:21]5)=[CH:18][CH:17]=[C:16]([O:26][CH3:27])[C:14]=4[N:15]=3)=[N:10][C:5]2=[CH:4][CH:3]=1.[OH:28][CH:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1.[CH3:35]CN(C(C)C)C(C)C.CN1[C:49](=[O:50])CCC1>CN(C1C=CN=CC=1)C>[CH3:35][O:50][CH2:49][N:8]1[C:6]2=[N:7][C:2]([N:32]3[CH2:33][CH2:34][CH:29]([OH:28])[CH2:30][CH2:31]3)=[CH:3][CH:4]=[C:5]2[N:10]=[C:9]1[C:11]1[S:12][C:13]2[C:19]([N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)=[CH:18][CH:17]=[C:16]([O:26][CH3:27])[C:14]=2[N:15]=1

Participants

6

Reactant 4

HCID 13387N-methyl-2-pyrrolidoneHCID 79341Piperidin-4-olHCID 81531DiisopropylethylamineHCID 178491999HCID 178491999, compound

Product 1

HCID 21919247HCID 21919247, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Conditions

Temperature
120 °C

Procedure

0.05 g 5-Chloro-2-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-3H-imidazo[4,5-b]pyridine (0.11 mmol), 0.034 g 4-hydroxypiperidine (0.34 mmol), 1 mg DMAP and 0.4 ml Hünigs base (2.2 mmol) were dissolved in NMP (1 ml). After stirring for 72 h at 120° C., the reaction mixture was concentrated and the residue taken up in water. A precipitation formed, which was filtered and dried in vacuo to yield 0.04 g 1-[3-methoxymethyl-2-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-3H-imidazo[4,5-b]pyridin-5-yl]-piperidin-4-ol (70%) as a light brown solid; M.p.: 120–130° C.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. customA precipitation
  3. customformed
  4. filtrationwhich was filtered
  5. customdried in vacuo

Sources & evidence

ORD record
ord-23ac63f6ae5849f792a206574363a4c4
Source dataset
uspto-grants-2006_10
Patent number
US07122545B2

Reaction notes

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