Dimethylformamide → N-(1-isobutoxyethoxy) 2-[5-(naphthalene-2-sulfonyl)-hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl]-pyrimidine-5-carboxamide
Reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[S:11]([N:14]1[CH2:18][CH:17]2[CH2:19][N:20]([C:22]3[N:27]=[CH:26][C:25]([C:28]([OH:30])=O)=[CH:24][N:23]=3)[CH2:21][CH:16]2[CH2:15]1)(=[O:13])=[O:12].CCN=C=N[CH2:36][CH2:37][CH2:38]N(C)C.Cl.C1C=CC2[N:51]([OH:52])N=NC=2C=1.CCN([CH:59]([CH3:61])C)C(C)C.CN([CH:65]=[O:66])C>>[CH2:65]([O:66][CH:59]([O:52][NH:51][C:28]([C:25]1[CH:26]=[N:27][C:22]([N:20]2[CH2:21][CH:16]3[CH:17]([CH2:18][N:14]([S:11]([C:2]4[CH:3]=[CH:4][C:5]5[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=5)[CH:1]=4)(=[O:13])=[O:12])[CH2:15]3)[CH2:19]2)=[N:23][CH:24]=1)=[O:30])[CH3:61])[CH:37]([CH3:36])[CH3:38]Participants
6
Reactant 5
Product 1
Procedure
To a solution of 2-[5-(naphthalene-2-sulfonyl)-hexahydro-pyrrolo[3,4-c]pyrrol-2-yl]-pyrimidine-5-carboxylic acid (0.266 g, 0.71 mmol) in DMF (2 ml) was added EDCl (0.204 g, 1.06 mmol), HOBt (0.171 g, 1.1 mmol), intermediate D (1 ml, 7 mmol) and DIPEA (2 ml, 11 mmol). The reaction was stirred for 24 h, then loaded directly onto a silica gel column. The product was eluted with 2% MeOH/DCM to 5% MeOH/DCM to yield the title compound (0.255 g, 66%). This was carried onto the next step without characterisation.
Workup
- washThe product was eluted with 2% MeOH/DCM to 5% MeOH/DCM
Sources & evidence
- ORD record
- ord-15d1de159709467c84d0c9b06d6e656d
- Source dataset
- uspto-grants-2011_04
- Patent number
- US07932246B2
Reaction notes
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