N-(4-amino-5-(quinolin-3-yl)-6,7,8,9-tetrahydropyrimido[5,4-b]indolizin-8-yl)acrylamide → Tas-121
Reaction equation
[NH2:1][C:2]1[C:7]2[C:8]([C:20]3[CH:21]=[N:22][C:23]4[C:28]([CH:29]=3)=[CH:27][CH:26]=[CH:25][CH:24]=4)=[C:9]3[N:14]([C:6]=2[N:5]=[CH:4][N:3]=1)[CH2:13][CH:12]([NH:15][C:16](=[O:19])[CH:17]=[CH2:18])[CH2:11][CH2:10]3>CCCCCC.C(O)C.C(N(CC)CC)C>[NH2:1][C:2]1[C:7]2[C:8]([C:20]3[CH:21]=[N:22][C:23]4[C:28]([CH:29]=3)=[CH:27][CH:26]=[CH:25][CH:24]=4)=[C:9]3[N:14]([C:6]=2[N:5]=[CH:4][N:3]=1)[CH2:13][C@H:12]([NH:15][C:16](=[O:19])[CH:17]=[CH2:18])[CH2:11][CH2:10]3.[NH2:1][C:2]1[C:7]2[C:8]([C:20]3[CH:21]=[N:22][C:23]4[C:28]([CH:29]=3)=[CH:27][CH:26]=[CH:25][CH:24]=4)=[C:9]3[N:14]([C:6]=2[N:5]=[CH:4][N:3]=1)[CH2:13][C@@H:12]([NH:15][C:16](=[O:19])[CH:17]=[CH2:18])[CH2:11][CH2:10]3Participants
4
Reactant 1
Product 2
Reagents, catalysts & solvents 1
Procedure
N-(4-amino-5-(quinolin-3-yl)-6,7,8,9-tetrahydropyrimido[5,4-b]indolizin-8-yl)acrylamide (197 mg) obtained in Step 12 was subjected to optical resolution using a column for optical resolution (CHIRALPAK AD-H 20 mm×250 mm, manufactured by Daicel Chemical Industries, Ltd.), mobile phase: hexane/ethanol/triethylamine, 50:50:0.1, flow rate: 10 ml/min) to obtain 72.4 mg of enantiomer A (retention time: 15.4 min, (R)-N-(4-amino-5-(quinolin-3-yl)-6,7,8,9-tetrahydropyrimido[5,4-b]indolizin-8-yl)acrylamide (Compound I-1)) and 78.3 mg of enantiomer B (retention time: 32.5 min, (S)-N-(4-amino-5-(quinolin-3-yl)-6,7,8,9-tetrahydropyrimido[5,4-b]indolizin-8-yl)acrylamide (Compound I-2)) as a light-yellow solid.
Sources & evidence
- ORD record
- ord-1efb55726f48432c8a59bee954a78055
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08889666B2
Reaction notes
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