N,N-Dimethylpiperidin-4-amine → HCID 67384948, compound

HRID 912204Notes

Reaction equation

HRID 912204 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([N:8]2[C:12]3[N:13]=[C:14]([N:42]4[CH2:47][CH2:46][O:45][CH2:44][CH2:43]4)[N:15]=[C:16]([C:17]4[CH:18]=[N:19][C:20]([N:23]([CH2:33][C:34]5[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][CH:35]=5)[CH2:24][C:25]5[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=5)=[N:21][CH:22]=4)[C:11]=3[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH3:48][N:49]([CH3:56])[CH:50]1[CH2:55][CH2:54][NH:53][CH2:52][CH2:51]1>>[CH3:32][O:31][C:28]1[CH:29]=[CH:30][C:25]([CH2:24][N:23]([CH2:33][C:34]2[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][CH:35]=2)[C:20]2[N:19]=[CH:18][C:17]([C:16]3[C:11]4[CH2:10][CH2:9][N:8]([C:5]5[CH:4]=[CH:3][C:2]([N:53]6[CH2:54][CH2:55][CH:50]([N:49]([CH3:56])[CH3:48])[CH2:51][CH2:52]6)=[N:7][CH:6]=5)[C:12]=4[N:13]=[C:14]([N:42]4[CH2:47][CH2:46][O:45][CH2:44][CH2:43]4)[N:15]=3)=[CH:22][N:21]=2)=[CH:26][CH:27]=1

Participants

3

Reactant 2

HCID 417391N,N-Dimethylpiperidin-4-amineHCID 59244926HCID 59244926, compound

Product 1

HCID 67384948HCID 67384948, compoundYield 85.5%

Procedure

Using {5-[7-(6-chloro-pyridin-3-yl)-2-morpholin-4-yl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl]-pyrimidin-2-yl}-bis-(4-methoxy-benzyl)-amine (200 mg, 0.31 mmol) obtained in Step A in Example 1-D-48 and 4-dimethylaminopiperidine (59 mg, 0.46 mmol) instead of N,N,N′-trimethyl ethylenediamine, in the same manner as Example 1-D-48, amination was carried out, to obtain a crude product of [5′-(4-{2-[bis-(4-methoxy-benzyl)-amino]-pyrimidin-5-yl}-2-morpholin-4-yl-5,6-dihydro-pyrrolo[2,3-d]pyrimidin-7-yl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-yl]-dimethyl-amine as a yellow solid (197 mg), and then the PMB groups were removed according to the above Deprotection method 2, to obtain the desired compound (D-73) as a yellow powder (32 mg, 24%).

Sources & evidence

ORD record
ord-ae8dda9fad2342809284c8e656e3ac68
Source dataset
uspto-grants-2011_09
Patent number
US08022205B2

Reaction notes

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