1-Methylpiperazine → HCID 59244618, compound

HRID 912273Notes

Reaction equation

HRID 912273 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.CN1CCNCC1.[CH3:59][N:60]([C:103]1[CH:108]=[CH:107][C:106]([N:109]2[CH2:114][CH2:113][N:112]([CH3:115])[CH2:111][CH2:110]2)=[CH:105][CH:104]=1)[C:61]([N:63]1[C:67]2[N:68]=[C:69]([N:97]3[CH2:102][CH2:101][O:100][CH2:99][CH2:98]3)[N:70]=[C:71]([C:72]3[CH:73]=[N:74][C:75]([N:78](CC4C=CC(OC)=CC=4)CC4C=CC(OC)=CC=4)=[N:76][CH:77]=3)[C:66]=2[CH2:65][CH2:64]1)=[O:62]>>[CH3:59][N:60]([C:103]1[CH:104]=[CH:105][C:106]([N:109]2[CH2:110][CH2:111][N:112]([CH3:115])[CH2:113][CH2:114]2)=[CH:107][CH:108]=1)[C:61]([N:63]1[C:67]2[N:68]=[C:69]([N:97]3[CH2:102][CH2:101][O:100][CH2:99][CH2:98]3)[N:70]=[C:71]([C:72]3[CH:73]=[N:74][C:75]([NH2:78])=[N:76][CH:77]=3)[C:66]=2[CH2:65][CH2:64]1)=[O:62]

Participants

4

Reactant 3

HCID 531671-MethylpiperazineHCID 59244797HCID 59244797, compoundHCID 67386186HCID 67386186, compound

Product 1

HCID 59244618HCID 59244618, compoundYield 63%

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 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 1-methyl-piperazine (35.7 μl) 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-(4-methyl-piperazin-1-yl)-phenyl]-amide was obtained. The PMB groups were removed according to Deprotection method 3, to obtain the desired compound (D-160) as a brown solid (54 mg, 63%).

Workup

  1. customThe PMB groups were removed

Sources & evidence

ORD record
ord-acf1529365e04a68b1ababfd332cce5f
Source dataset
uspto-grants-2011_09
Patent number
US08022205B2

Reaction notes

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