N-(tert-butoxycarbonyl)glycine → tert-butyl N-[2-[4-(2-methyl-4-nitro-pyrazol-3-yl)-1,4-diazepan-1-yl]-2-oxo-ethyl]carbamate
Reaction equation
NC1SC(C2C(F)=CC=CC=2F)=NC=1C(NC1C=NN(C)C=1N1CCCN(C2CNC2)CC1)=O.[CH3:35][N:36]1[C:40]([N:41]2[CH2:47][CH2:46][CH2:45][NH:44][CH2:43][CH2:42]2)=[C:39]([N+:48]([O-:50])=[O:49])[CH:38]=[N:37]1.[C:51]([O:55][C:56]([NH:58][CH2:59][C:60](O)=[O:61])=[O:57])([CH3:54])([CH3:53])[CH3:52].C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>C(Cl)Cl>[CH3:35][N:36]1[C:40]([N:41]2[CH2:47][CH2:46][CH2:45][N:44]([C:60](=[O:61])[CH2:59][NH:58][C:56](=[O:57])[O:55][C:51]([CH3:52])([CH3:53])[CH3:54])[CH2:43][CH2:42]2)=[C:39]([N+:48]([O-:50])=[O:49])[CH:38]=[N:37]1Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
In the preparation of 362, 1-(2-methyl-4-nitro-pyrazol-3-yl)-1,4-diazepane (105 mg, 0.47 mmol), 2-(tert-butoxycarbonylamino)acetic acid (106 mg, 0.61 mmol) and PyBOP (396 mg, 0.75 mmol) were dissolved in DCM (6 mL). DIPEA (0.49 ml, 2.80 mmol) was added and the mixture was stirred at room temperature for 18 h. The crude reaction mixture was concentrated and the residue was purified via silica gel column chromatography (0-100% EA/heptane) to gave tert-butyl N-[2-[4-(2-methyl-4-nitro-pyrazol-3-yl)-1,4-diazepan-1-yl]-2-oxo-ethyl]carbamate (qualitative yield).
Workup
- customThe crude reaction mixture
- concentrationwas concentrated
- customthe residue was purified via silica gel column chromatography (0-100% EA/heptane)
Sources & evidence
- ORD record
- ord-e1e2c73a3895455480d84bd8cf885542
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08614206B2
Reaction notes
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