Diisopropylethylamine → N-{1-[6-Amino-2-(methylsulfanyl)-4-pyrimidinyl]-4-piperidinyl}-3,4-dichloro-5-methyl-1H-pyrrole-2-carboxamide
Reaction equation
C(N(C(C)C)CC)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[Cl:34][C:35]1[C:39]([Cl:40])=[C:38]([CH3:41])[NH:37][C:36]=1[C:42](NC1CCN(C2C=C(C3N=CON=3)C=C(Cl)N=2)CC1)=[O:43].Cl.[NH2:64][CH:65]1[CH2:70][CH2:69][N:68]([C:71]2[N:76]=[C:75]([S:77][CH3:78])[N:74]=[C:73]([NH2:79])[CH:72]=2)[CH2:67][CH2:66]1>CN(C=O)C>[NH2:79][C:73]1[N:74]=[C:75]([S:77][CH3:78])[N:76]=[C:71]([N:68]2[CH2:69][CH2:70][CH:65]([NH:64][C:42]([C:36]3[NH:37][C:38]([CH3:41])=[C:39]([Cl:40])[C:35]=3[Cl:34])=[O:43])[CH2:66][CH2:67]2)[CH:72]=1Participants
6
Reactant 4
HCID 81531Diisopropylethylamine
HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)
HCID 685798436-(4-Aminopiperidin-1-yl)-2-(methylthio)pyrimidin-4-amine hydrochloride2×
HCID 866083163,4-Dichloro-N-{1-[6-chloro-4-(1,2,4-oxadiazol-3-yl)-2-pyridinyl]-4-piperidinyl}-5-methyl-1H-pyrrole-2-carboxamide2×Product 1
Reagents, catalysts & solvents 1
Procedure
Diisopropylethylamine (0.21 ml, 1.25 mmol) and HATU (0.239 g, 0.63 mmol) were added to a stirred solution of 3,4-dichloro-5-methyl-1H-pyrrole-2-carboxylic acid (Intermediate 3) (0.122 g, 0.63 mmol) in DMF (2 ml). The resultant solution was stirred for 5 minutes, 6-(4-amino-piperidin-1-yl)-2-(methylthio)pyrimidin-4-amine hydrochloride (Intermediate 46) (0.2 g, 0.63 mmol) was added and the mixture was stirred at room temperature for 18 h. The crude mixture was filtered and purified by semi-preparative HPLC eluting with CH3CN/H2O (0.1% TFA) to give the title product (42 mg).
Workup
- filtrationThe crude mixture was filtered
- custompurified by semi-preparative HPLC
- washeluting with CH3CN/H2O (0.1% TFA)
Sources & evidence
- ORD record
- ord-13b1baf489a54e23bac8b226265dd65f
- Source dataset
- uspto-grants-2010_05
- Patent number
- US07709503B2
Reaction notes
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