Triethylamine → Tert-butyl 5-(5-(5-chloropicolinamido)-2-fluorophenyl)-6,6-difluoro-5-methyl-2,5,6,7-tetrahydro-1,4-oxazepin-3-ylcarbamate
Reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([OH:10])=O)=[N:6][CH:7]=1.CCN(CC)CC.CCN=C=NCCCN(C)C.Cl.C1C=NC2N(O)N=NC=2C=1.[NH2:40][C:41]1[CH:42]=[CH:43][C:44]([F:65])=[C:45]([C:47]2([CH3:64])[C:53]([F:55])([F:54])[CH2:52][O:51][CH2:50][C:49]([NH:56][C:57](=[O:63])[O:58][C:59]([CH3:62])([CH3:61])[CH3:60])=[N:48]2)[CH:46]=1.C(OC(C)(C)C)=O>CN(C=O)C.CCCCCC.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([NH:40][C:41]2[CH:42]=[CH:43][C:44]([F:65])=[C:45]([C:47]3([CH3:64])[C:53]([F:54])([F:55])[CH2:52][O:51][CH2:50][C:49]([NH:56][C:57](=[O:63])[O:58][C:59]([CH3:60])([CH3:62])[CH3:61])=[N:48]3)[CH:46]=2)=[O:10])=[N:6][CH:7]=1Participants
10
Reactant 6
HCID 8471Triethylamine
HCID 61207tert-Butyl Formate
HCID 181649HOAt
HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride
HCID 27628725-Chloro-2-picolinic acid
HCID 66666055Tert-butyl 5-(5-amino-2-fluorophenyl)-6,6-difluoro-5-methyl-2,5,6,7-tetrahydro-1,4-oxazepin-3-ylcarbamateProduct 1
Reagents, catalysts & solvents 3
Procedure
To a solution of 5-Chloro-pyridine-2-carboxylic acid (0.085 g, 0.54 mmol) in dry DMF (3.0 mL), Et3N (0.22 mL, 1.6 mmol) and EDCl (0.128 mg, 0.81 mmol) and HOAt (0.11 g, 0.81 mmol) and tert-butyl 5-(5-amino-2-fluorophenyl)-6,6-difluoro-5-methyl-2,5,6,7-tetrahydro-1,4-oxazepin-3-ylcarbamate (0.201 g, 0.54 mmol) were added and stirred at rt for 24 h. upon completion of the reaction, reaction mixture was poured into a rapidly stirred ice cold water to obtain precipitate. Yield=220 mg, (80%). TLC (30% ethyl acetate in Hexane): Rf=0.4, LCMS: RtH8=1.78 [M+H-Boc]+=413.0, 414.8,
Workup
- additionwas poured into a rapidly stirred ice cold water
- customto obtain precipitate
Sources & evidence
- ORD record
- ord-efc12cc61aab407d9772aa4d85c26d25
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08338413B1
Reaction notes
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