1-(2-Hydroxyethyl)piperazine → HCID 59244908, compound

HRID 912281Notes

Reaction equation

HRID 912281 reaction equation
COC1C=CC(C[N:8](CC2C=CC(OC)=CC=2)[C:9]2[N:14]=[CH:13][C:12]([C:15]3[C:16]4[CH2:29][CH2:28][N:27]([C:30]5[CH:35]=[CH:34][C:33]([CH2:36][CH2:37][C:38](O)=[O:39])=[CH:32][CH:31]=5)[C:17]=4[N:18]=[C:19]([N:21]4[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)[N:20]=3)=[CH:11][N:10]=2)=CC=1.[N:52]1([CH2:58][CH2:59][OH:60])[CH2:57][CH2:56][NH:55][CH2:54][CH2:53]1>>[NH2:8][C:9]1[N:14]=[CH:13][C:12]([C:15]2[C:16]3[CH2:29][CH2:28][N:27]([C:30]4[CH:35]=[CH:34][C:33]([CH2:36][CH2:37][C:38]([N:55]5[CH2:56][CH2:57][N:52]([CH2:58][CH2:59][OH:60])[CH2:53][CH2:54]5)=[O:39])=[CH:32][CH:31]=4)[C:17]=3[N:18]=[C:19]([N:21]3[CH2:22][CH2:23][O:24][CH2:25][CH2:26]3)[N:20]=2)=[CH:11][N:10]=1

Participants

3

Reactant 2

HCID 76771-(2-Hydroxyethyl)piperazineHCID 59244857HCID 59244857, compound

Product 1

HCID 59244908HCID 59244908, compoundYield 25%

Procedure

Using 3-[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)-phenyl]-propionic acid (100 mg) obtained in Step A in Example 1-D-168 and 2-piperazin-1-yl-ethanol (23 mg) instead of 3-(aminomethyl)pyridine, in the same manner as Step B in Example 1-D-19, 3-[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)-phenyl]-1-[4-(2-hydroxy-ethyl)-piperazin-1-yl]-propan-1-one was obtained, and then the PMB groups were removed according to the above Deprotection method 2, to obtain the desired compound (D-170) as a pale yellow powder (20 mg, 25%).

Workup

  1. customthe PMB groups were removed

Sources & evidence

ORD record
ord-fbf3e305fc05442a8721a113777e7490
Source dataset
uspto-grants-2011_09
Patent number
US08022205B2

Reaction notes

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