3-(1-aminoethyl)-4-(5-(morpholinomethyl)thiophen-2-yl)-1H-isochromen-1-one dihydrochloride → 4-(5-(morpholinomethyl)thiophen-2-yl)-3-(1-(thieno[3,2-d]pyrimidin-4-ylamino)ethyl)-1H-isochromen-1-one hydrochloride
Reaction equation
[ClH:1].N1C=C([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10](=[O:17])[O:9][C:8]=2[CH:18]([NH:20][C:21]2[C:22]3[S:29][CH:28]=[CH:27][C:23]=3[N:24]=[CH:25][N:26]=2)[CH3:19])C=N1.Cl.Cl.[NH2:32][CH:33]([C:35]1[O:36][C:37](=[O:57])[C:38]2[C:43]([C:44]=1[C:45]1[S:46][C:47]([CH2:50][N:51]3[CH2:56][CH2:55][O:54][CH2:53][CH2:52]3)=[CH:48][CH:49]=1)=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH3:34]>>[ClH:1].[ClH:1].[NH2:32][CH:33]([C:35]1[O:36][C:37](=[O:57])[C:38]2[C:43]([C:44]=1[C:45]1[S:46][C:47]([CH2:50][N:51]3[CH2:56][CH2:55][O:54][CH2:53][CH2:52]3)=[CH:48][CH:49]=1)=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH3:34].[Cl:1][C:21]1[C:22]2[S:29][CH:28]=[CH:27][C:23]=2[N:24]=[CH:25][N:26]=1.[ClH:1].[O:54]1[CH2:55][CH2:56][N:51]([CH2:50][C:47]2[S:46][C:45]([C:7]3[C:16]4[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=4)[C:10](=[O:17])[O:9][C:8]=3[CH:18]([NH:20][C:21]3[C:22]4[S:29][CH:28]=[CH:27][C:23]=4[N:24]=[CH:25][N:26]=3)[CH3:19])=[CH:49][CH:48]=2)[CH2:52][CH2:53]1Participants
5
Reactant 2
Product 3
Procedure
The title compound was made in a similar way as that of the compound of example 80, from 3-(1-aminoethyl)-4-(5-(morpholinomethyl)thiophen-2-yl)-1H-isochromen-1-one dihydrochloride (Intermediate E3, 80 mg, 0.180 mmol) and 4-chlorothieno[3,2-d]pyrimidine (43.1 mg, 0.253 mmol) to give the title compound (52 mg, 53.3%) as yellowish solid.
Sources & evidence
- ORD record
- ord-6542c7e4af644f7d8b51b4692746d068
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09321776B2
Reaction notes
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