tert-Butyl piperazine-1-carboxylate → HCID 59244788, compound

HRID 912274Notes

Reaction equation

HRID 912274 reaction equation
BrC1C=CC(N(C)C(N2C3N=C(N4CCOCC4)N=C(C4C=NC(N(CC5C=CC(OC)=CC=5)CC5C=CC(OC)=CC=5)=NC=4)C=3CC2)=O)=CC=1.C(N1CCNCC1)(OC(C)(C)C)=O.[CH3:65][N:66]([C:109]1[CH:114]=[CH:113][C:112]([N:115]2[CH2:120][CH2:119][NH:118][CH2:117][CH2:116]2)=[CH:111][CH:110]=1)[C:67]([N:69]1[C:73]2[N:74]=[C:75]([N:103]3[CH2:108][CH2:107][O:106][CH2:105][CH2:104]3)[N:76]=[C:77]([C:78]3[CH:79]=[N:80][C:81]([N:84](CC4C=CC(OC)=CC=4)CC4C=CC(OC)=CC=4)=[N:82][CH:83]=3)[C:72]=2[CH2:71][CH2:70]1)=[O:68]>>[CH3:65][N:66]([C:109]1[CH:110]=[CH:111][C:112]([N:115]2[CH2:116][CH2:117][NH:118][CH2:119][CH2:120]2)=[CH:113][CH:114]=1)[C:67]([N:69]1[C:73]2[N:74]=[C:75]([N:103]3[CH2:108][CH2:107][O:106][CH2:105][CH2:104]3)[N:76]=[C:77]([C:78]3[CH:79]=[N:80][C:81]([NH2:84])=[N:82][CH:83]=3)[C:72]=2[CH2:71][CH2:70]1)=[O:68]

Participants

4

Reactant 3

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 59244797HCID 59244797, compoundHCID 67385285HCID 67385285, compound

Product 1

HCID 59244788HCID 59244788, compoundYield 67%

Procedure

Using 4-{2-[bis-(4-methoxy-benzyl)-amino]-pyrimidin-5-yl}-2-morpholin-4-yl-5,6-dihydro-pyrrolo[2,3-d]pyrimidine-7-carboxylic acid (4-bromo-phenyl)-methyl-amide (121 mg) obtained in Step B in Example 1-D-160 instead of 4-{2-[bis-(4-methoxy-benzyl)-amino]-pyrimidin-5-yl}-2-morpholin-4-yl-5,6-dihydro-pyrrolo[2,3-d]pyrimidine-7-carboxylic acid (3-bromo-phenyl)-methyl-amide, and N-Boc-piperazine (60 mg) instead of 2-piperazin-1-yl-ethanol, in the same manner as Step C in Example 1-D-153, a crude product of 4-{2-[bis-(4-methoxy-benzyl)-amino]-pyrimidin-5-yl}-2-morpholin-4-yl-5,6-dihydro-pyrrolo[2,3-d]pyrimidine-7-carboxylic acid methyl-(4-piperazin-1-yl-phenyl)-amide was obtained. The PMB groups were removed according to Deprotection method 3, to obtain the desired compound (D-161) as a yellow solid (56.1 mg, 67%).

Workup

  1. customThe PMB groups were removed

Sources & evidence

ORD record
ord-1e4ab669fcfc44269d182241b6170ea1
Source dataset
uspto-grants-2011_09
Patent number
US08022205B2

Reaction notes

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