1-Methylpiperazine → HCID 59244573, compound

HRID 912335Notes

Reaction equation

HRID 912335 reaction equation
COC1C=CC(CN(CC2C=CC(OC)=CC=2)C2N=CC(C3C4CCNC=4N=C(N4CCOCC4)N=3)=CN=2)=CC=1.NC1C(C)=C(C(N2CCN(C)CC2)=O)C=CC=1.CN1CCNCC1.CC1C=CC(N2CCOCC2)=CC=1N.[CH3:79][C:80]1[C:85]([C:86]([N:88]2[CH2:93][CH2:92][N:91]([CH3:94])[CH2:90][CH2:89]2)=[O:87])=[CH:84][CH:83]=[CH:82][C:81]=1[NH:95][C:96]([N:98]1[C:102]2[N:103]=[C:104]([N:132]3[CH2:137][CH2:136][O:135][CH2:134][CH2:133]3)[N:105]=[C:106]([C:107]3[CH:108]=[N:109][C:110]([N:113](CC4C=CC(OC)=CC=4)CC4C=CC(OC)=CC=4)=[N:111][CH:112]=3)[C:101]=2[CH2:100][CH2:99]1)=[O:97]>>[CH3:79][C:80]1[C:85]([C:86]([N:88]2[CH2:93][CH2:92][N:91]([CH3:94])[CH2:90][CH2:89]2)=[O:87])=[CH:84][CH:83]=[CH:82][C:81]=1[NH:95][C:96]([N:98]1[C:102]2[N:103]=[C:104]([N:132]3[CH2:137][CH2:136][O:135][CH2:134][CH2:133]3)[N:105]=[C:106]([C:107]3[CH:108]=[N:109][C:110]([NH2:113])=[N:111][CH:112]=3)[C:101]=2[CH2:100][CH2:99]1)=[O:97]

Participants

6

Reactant 5

HCID 531671-MethylpiperazineHCID 16770955HCID 16770955, compoundHCID 392386232-Methyl-5-morpholinoanilineHCID 45258862Bis-(4-methoxybenzyl)-[5-(2-morpholin-4-yl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl)-pyrimidin-2-yl]-amineHCID 86640138HCID 86640138, compound

Product 1

HCID 59244573HCID 59244573, compoundYield 29%

Procedure

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 (150 mg), and (3-amino-2-methyl-phenyl)-(4-methyl-piperazin-1-yl)-methanone (71 mg) obtained using 1-methyl-piperazine instead of morpholine in the same manner as Step A and Step B in Example 1-D-243, instead of 2-methyl-5-morpholin-4-yl-phenylamine, in the same manner as Step C in Example 1-D-237, 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 [2-methyl-3-(4-methyl-piperazine-1-carbonyl)-phenyl]-amide was obtained as a crude product. The PMB groups were removed according to Deprotection method 2, to obtain the desired compound (D-244) (45 mg, 29%).

Workup

  1. customobtained
  2. customThe PMB groups were removed

Sources & evidence

ORD record
ord-ed8e5fb4f3ae486c97cb8e44d1f83f32
Source dataset
uspto-grants-2011_09
Patent number
US08022205B2

Reaction notes

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