3-(Methylaminomethyl)pyridine → HCID 67385507, compound
Reaction equation
[CH3:1][O:2][C:3]1[CH:50]=[CH:49][C:6]([CH2:7][N:8]([CH2:40][C:41]2[CH:46]=[CH:45][C:44]([O:47][CH3:48])=[CH:43][CH:42]=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:38]=[CH:37][C:33]([C:34]([OH:36])=O)=[CH:32][C:31]=5[F:39])[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)=[CH:5][CH:4]=1.[CH3:51][NH:52][CH2:53][C:54]1[CH:55]=[N:56][CH:57]=[CH:58][CH:59]=1>>[CH3:48][O:47][C:44]1[CH:43]=[CH:42][C:41]([CH2:40][N:8]([CH2:7][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:50][CH:49]=2)[C:9]2[N:10]=[CH:11][C:12]([C:15]3[C:16]4[CH2:29][CH2:28][N:27]([C:30]5[CH:38]=[CH:37][C:33]([C:34]([N:52]([CH3:51])[CH2:53][C:54]6[CH:55]=[N:56][CH:57]=[CH:58][CH:59]=6)=[O:36])=[CH:32][C:31]=5[F:39])[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:13][N:14]=2)=[CH:46][CH:45]=1Participants
Procedure
Using 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)-3-fluoro-benzoic acid (80.0 mg, 0.118 mmol) obtained in Step A in Example 1-D-21 and N-methyl-N-(3-pyridylmethyl)amine (21.6 mg, 0.177 mmol) instead of 1-pyridine-3-yl-piperazine, the amidation was carried out in the same manner as Step B in Example 1-D-21, to obtain a crude product of 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)-3-fluoro-N-methyl-N-pyridin-3-ylmethyl-benzamide as a yellow solid (92.8 mg), and then the PMB groups were removed according to the above Deprotection method 3, to obtain the desired compound (D-318) as a yellow powder (38.0 mg, 59%).
Sources & evidence
- ORD record
- ord-d83151ffaddc473fa6eb344a66c6397a
- Source dataset
- uspto-grants-2011_09
- Patent number
- US08022205B2
Reaction notes
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