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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

HRID 1915931
Notes
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Reaction equation

HRID 1915931 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]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 78288N-(tert-butoxycarbonyl)glycineHCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 749832175-amino-N-[5-[4-(azetidin-3-yl)-1,4-diazepan-1-yl]-1-methyl-pyrazol-4-yl]-2-(2,6-difluorophenyl)thiazole-4-carboxamideHCID 866801231-(2-Methyl-4-nitro-pyrazol-3-yl)-1,4-diazepane

Product 1

HCID 86680130
tert-butyl N-[2-[4-(2-methyl-4-nitro-pyrazol-3-yl)-1,4-diazepan-1-yl]-2-oxo-ethyl]carbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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

  1. customThe crude reaction mixture
  2. concentrationwas concentrated
  3. 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
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08614206B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes