tert-Butyl piperazine-1-carboxylate → HCID 67386241, compound
Reaction equation
[CH3:1][O:2][C:3]1[CH:49]=[CH:48][C:6]([CH2:7][N:8]([CH2:39][C:40]2[CH:45]=[CH:44][C:43]([O:46][CH3:47])=[CH:42][CH:41]=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][CH:31]=5)[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.[C:50]([N:57]1[CH2:62][CH2:61][NH:60][CH2:59][CH2:58]1)([O:52][C:53]([CH3:56])([CH3:55])[CH3:54])=[O:51]>>[C:53]([O:52][C:50]([N:57]1[CH2:62][CH2:61][N:60]([C:34](=[O:36])[C:33]2[CH:32]=[CH:31][C:30]([N:27]3[C:17]4[N:18]=[C:19]([N:21]5[CH2:26][CH2:25][O:24][CH2:23][CH2:22]5)[N:20]=[C:15]([C:12]5[CH:13]=[N:14][C:9]([N:8]([CH2:39][C:40]6[CH:41]=[CH:42][C:43]([O:46][CH3:47])=[CH:44][CH:45]=6)[CH2:7][C:6]6[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:49][CH:48]=6)=[N:10][CH:11]=5)[C:16]=4[CH2:29][CH2:28]3)=[CH:38][CH:37]=2)[CH2:59][CH2:58]1)=[O:51])([CH3:56])([CH3:54])[CH3:55]Participants
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)-benzoic acid (70.4 mg, 0.107 mmol) obtained in Step A in Example 1-D-19 and 1-Boc-piperazine (31.7 mg, 0.170 mmol) instead of 3-(aminomethyl)pyridine, in the same manner as Step B in Example 1-D-19, amidation was carried out, to obtain a crude product of 4-{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]-benzoyl}-piperazine-1-carboxylic acid tert-butyl ester as a yellow solid (74.2 mg), and then the PMB groups and BOC group were removed according to the above Deprotection method 3, to obtain the desired compound (D-112) as a colorless powder (41.4 mg, 80%).
Sources & evidence
- ORD record
- ord-0f1392d0c71e4c89aca38bf80c0af649
- Source dataset
- uspto-grants-2011_09
- Patent number
- US08022205B2
Reaction notes
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