Water → HCID 87336222, compound

HRID 1696247Notes

Reaction equation

HRID 1696247 reaction equation
[CH3:1][C@@H:2]1[CH2:7][CH2:6][NH:5][CH2:4][C@@H:3]1[N:8]1[C:12]2=[C:13]3[CH:19]=[CH:18][NH:17][C:14]3=[N:15][CH:16]=[C:11]2[NH:10][C:9]1=[O:20].[Cl:21][C:22]1[N:27]=[C:26](Cl)[CH:25]=[CH:24][N:23]=1.C(N(CC)CC)C.O>C(O)C>[Cl:21][C:22]1[N:27]=[C:26]([N:5]2[CH2:6][CH2:7][C@@H:2]([CH3:1])[C@@H:3]([N:8]3[C:12]4=[C:13]5[CH:19]=[CH:18][NH:17][C:14]5=[N:15][CH:16]=[C:11]4[NH:10][C:9]3=[O:20])[CH2:4]2)[CH:25]=[CH:24][N:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 775312,4-DichloropyrimidineHCID 67277969HCID 67277969, compound

Product 1

HCID 87336222HCID 87336222, compoundYield 45.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To the mixture of rel-1-[(3R,4R)-4-methyl-3-piperidinyl]-3,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridin-2(1H)-one-(100 mg) and 2,4-dichloropyrimidine (82 mg) in ethanol (2 mL), triethylamine (75 mg) was added at ambient temperature. Then After the mixture was stirred at ambient temperature for 17 hours, water (10 mL) was added. The resulting precipitate was collected, to afford rel-1-[(3R,4R)-1-(2-chloro-4-pyrimidinyl)-4-methyl-3-piperidinyl]-3,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridin-2(1H)-one (65 mg) as yellow powder. From NMR, it was found that the obtained powder was mixture of regioisomer (4:1).

Workup

  1. additionwas added at ambient temperature
  2. customThe resulting precipitate was collected

Sources & evidence

ORD record
ord-e2347c4cc5784feea2f27f0b6949dc24
Source dataset
uspto-grants-2012_04
Patent number
US08163767B2

Reaction notes

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