1-(2-Hydroxyethyl)piperazine → HCID 43421970, compound

HRID 912305Notes

Reaction equation

HRID 912305 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8](Cl)=[O:9])[CH:3]=1.[OH:11][CH2:12][CH2:13][N:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1>>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([N:17]2[CH2:18][CH2:19][N:14]([CH2:13][CH2:12][OH:11])[CH2:15][CH2:16]2)=[O:9])[CH:3]=1

Participants

3

Reactant 2

HCID 76771-(2-Hydroxyethyl)piperazineHCID 110951464-chloropyridine-2-carbonyl Chloride

Product 1

HCID 43421970HCID 43421970, compound

Procedure

Using 4-chloropicolinic acid chloride and 4-(2-hydroxyethyl)piperazine instead of N-Boc-piperazine, amidation was carried out in the same manner as Step A in Example 1-D-199, to obtain (4-chloro-pyridin-2-yl)-[4-(2-hydroxy-ethyl)-piperazin-1-yl]-methanone. Using bis-(4-methoxy-benzyl)-[5-(2-morpholin-4-yl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl)-pyrimidin-2-yl]-amine (282 mg, 0.52 mmol), and (4-chloro-pyridin-2-yl)-[4-(2-hydroxy-ethyl)-piperazin-1-yl]-methanone (175 mg, 0.65 mmol) instead of 4-chloropicolinic acid t-butylamide, amination was carried out in the same manner as Example 1-D-07, to obtain a crude product of [4-(4-{2-[bis-(4-methoxy-benzyl)-amino]-pyrimidin-5-yl}-2-morpholin-4-yl-5,6-dihydro-pyrrolo[2,3-d]pyrimidin-7-yl)-pyridin-2-yl]-[4-(2-hydroxy-ethyl)-piperazin-1-yl]-methanone as a colorless solid (210 mg), and then the PMB groups were removed according to the above Deprotection method 2, to obtain the desired compound (D-202) as a colorless powder (114 mg, 80%).

Sources & evidence

ORD record
ord-45bca348cb0c48a3baefc8a0f9897879
Source dataset
uspto-grants-2011_09
Patent number
US08022205B2

Reaction notes

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