Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → 2-{[5-(Benzyloxy)-2-pyridinyl]methyl}-1-(cyclopropylmethyl)-1H-benzimidazole-5-carbonitrile
Reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][C:16](O)=O)=[N:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][C:27]=1[NH:28][CH2:29][CH:30]1[CH2:32][CH2:31]1)[C:23]#[N:24].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CC(O)=O>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][C:16]2[N:28]([CH2:29][CH:30]3[CH2:32][CH2:31]3)[C:27]3[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][C:20]=3[N:19]=2)=[N:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Following the general procedure 13B, 360 mg (1.48 mmol) of [5-(benzyloxy)-2-pyridinyl]acetic acid was coupled with 3-amino-4-[(Cyclopropylmethyl)amino]benzonitrile using HATU. The resulting intermediate was heated in HOAc (20 mL) at 90° C. overnight. After being concentrated, the crude residue was purified by silica gel column chromatography to afford the pure product (230 mg, 40% for 2 steps) as an oil. MS (ESI) (M+H)+=395.
Workup
- concentrationAfter being concentrated
- customthe crude residue was purified by silica gel column chromatography
- customto afford the pure product (230 mg, 40% for 2 steps) as an oil
Sources & evidence
- ORD record
- ord-b2f3bc69935a4feba2294ba25bfe3fcf
- Source dataset
- uspto-grants-2006_04
- Patent number
- US07030139B2
Reaction notes
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