Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate → HCID 22064664, compound

HRID 1828109Notes

Reaction equation

HRID 1828109 reaction equation
F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[CH2:28]([O:30][CH:31]([C:45]([O:47]CC)=O)[NH:32][C:33](=[O:44])[C:34]1[C:35](=[C:39]([F:43])[CH:40]=[CH:41][CH:42]=1)[C:36]([OH:38])=O)[CH3:29].C(OC(C(OCC)=O)NC(=O)C1C(=CC=CC=1F)C(O)=O)C.[NH2:72][CH2:73][C:74]1[CH:81]=[CH:80][C:77]([C:78]#[N:79])=[CH:76][C:75]=1[N+:82]([O-:84])=[O:83]>>[C:78]([C:77]1[CH:80]=[CH:81][C:74]([CH2:73][NH:72][C:45](=[O:47])[CH:31]([O:30][CH2:28][CH3:29])[N:32]2[C:36](=[O:38])[C:35]3[C:34](=[CH:42][CH:41]=[CH:40][C:39]=3[F:43])[C:33]2=[O:44])=[C:75]([N+:82]([O-:84])=[O:83])[CH:76]=1)#[N:79]

Participants

5

Reactant 4

HCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 21905720HCID 21905720, compoundHCID 22064636HCID 22064636, compoundHCID 22064681HCID 22064681, compound

Product 1

HCID 22064664HCID 22064664, compound

Procedure

According to general procedure C, but using 2.2 eq. of BOP coupling reagent and adding the amine component after a delay time of 1 h, (RS)-N-(ethoxy-ethoxycarbonyl-methyl)-6-fluoro-phthalamic acid and its regioisomer (RS)-N-(ethoxy-ethoxycarbonyl-methyl)-3-fluoro-phthalamic acid (example 35.2) was reacted with 4-aminomethyl-3-nitrobenzonitrile (CAS 701269-65-0) to give (RS)-N-(4-cyano-2-nitro-benzyl)-2-ethoxy-2-(4-fluoro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-acetamide as yellow viscous oil which was further processed as follows, MS 427.3 ([M+H]+).

Sources & evidence

ORD record
ord-3f75dda3f5da42b79d22dfbec472a3bc
Source dataset
uspto-grants-2006_06
Patent number
US07056932B2

Reaction notes

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