Water → 5-(2-Hydroxy-ethyl)-7-morpholin-4-yl-2-(2-quinolin-2-yl-ethyl)-3,5-dihydro-2H-pyrrolo[3,4-c]pyridine-1,6-dione

HRID 1752624Notes

Reaction equation

HRID 1752624 reaction equation
B(Br)(Br)Br.C[O:6][CH2:7][CH2:8][N:9]1[C:14](=[O:15])[C:13]([N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)=[C:12]2[C:22](=[O:37])[N:23]([CH2:25][CH2:26][C:27]3[CH:36]=[CH:35][C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[N:28]=3)[CH2:24][C:11]2=[CH:10]1.C(OCC)C.O>C(Cl)Cl>[OH:6][CH2:7][CH2:8][N:9]1[C:14](=[O:15])[C:13]([N:16]2[CH2:17][CH2:18][O:19][CH2:20][CH2:21]2)=[C:12]2[C:22](=[O:37])[N:23]([CH2:25][CH2:26][C:27]3[CH:36]=[CH:35][C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[N:28]=3)[CH2:24][C:11]2=[CH:10]1

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 25134Boron tribromideHCID 862960625-(2-Methoxy-ethyl)-7-morpholin-4-yl-2-(2-quinolin-2-yl-ethyl)-3,5-dihydro-2H-pyrrolo[3,4-c]pyridine-1,6-dione

Product 1

HCID 862960635-(2-Hydroxy-ethyl)-7-morpholin-4-yl-2-(2-quinolin-2-yl-ethyl)-3,5-dihydro-2H-pyrrolo[3,4-c]pyridine-1,6-dioneYield 41.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Boron tribromide (0.5 ml, 0.445 mmol) and 5-(2-methoxy-ethyl)-7-morpholin-4-yl-2-(2-quinolin-2-yl-ethyl)-3,5-dihydro-2H-pyrrolo[3,4-c]pyridine-1,6-dione (50 mg, 0.111 mmol, see Example 18) were dissolved in DCM (30 ml) in a round-bottomed flask. The reaction was stirred at about 0° C. for about 3 h, diethyl ether and afterwards water were added. The obtained crude material was purified by preparative HPLC to give the title compound (20 mg, 0.046 mmol, 41.3% yield).

Workup

  1. customThe obtained crude material
  2. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-5bf62d03fa9f4f3aacd9e69cb780ff00
Source dataset
uspto-grants-2015_10
Patent number
US09163019B2

Reaction notes

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