1-Hydroxybenzotriazole → 2-amino-N-(1-(1-oxo-4-phenyl-1H-isochromen-3-yl)ethyl)pyrazolo[1,5-a]pyrimidine-3-carboxamide
Reaction equation
Cl.[NH2:2][CH:3]([C:5]1[O:6][C:7](=[O:21])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH3:4].[NH2:22][C:23]1[C:31]([C:32](O)=[O:33])=[C:26]2[N:27]=[CH:28][CH:29]=[CH:30][N:25]2[N:24]=1.C1C=CC2N(O)N=NC=2C=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>C(Cl)Cl>[NH2:22][C:23]1[C:31]([C:32]([NH:2][CH:3]([C:5]2[O:6][C:7](=[O:21])[C:8]3[C:13]([C:14]=2[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH3:4])=[O:33])=[C:26]2[N:27]=[CH:28][CH:29]=[CH:30][N:25]2[N:24]=1Participants
7
Reactant 5
HCID 757711-Hydroxybenzotriazole
HCID 81531Diisopropylethylamine
HCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)
HCID 717429442-Aminopyrazolo[1,5-A]pyrimidine-3-carboxylic acid
HCID 1181314633-(1-aminoethyl)-4-phenyl-1H-isochromen-1-one hydrochloride2×Product 1
Reagents, catalysts & solvents 1
Procedure
3-(1-aminoethyl)-4-phenyl-1H-isochromen-1-one hydrochloride (intermediate E2, 50 mg, 0.166 mmol), 2-aminopyrazolo[1,5-a]pyrimidine-3-carboxylic acid (32.5 mg, 0.182 mmol), HOBt (30.4 mg, 0.199 mmol), HBTU (17.25 mg, 0.033 mmol) and DIPEA (61.0 μl, 0.349 mmol) were reacted in DCM (1 ml) at RT for 18 hrs. The crude was purified via reverse phase chromatography with a Biotage C18 30 g SNAP column (Phase A, water 95%, ACN 5%, formic acid 0.1%); Phase B ACN 95%, water 5%, formic acid 0.1%) to give the title compound (20 mg, 28%).
Workup
- customThe crude was purified via reverse phase chromatography with a Biotage C18 30 g SNAP column (Phase A, water 95%, ACN 5%, formic acid 0.1%)
Sources & evidence
- ORD record
- ord-9f27113e43bb4a8d98415ea5bcac342c
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09321776B2
Reaction notes
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