Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → HCID 178507354, compound

HRID 1368002Notes

Reaction equation

HRID 1368002 reaction equation
O.C1C2C(=CC=CC=2)C=C(C(O)=O)N=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[N+](C1C=CC2NC(N)=NC=2C=1)([O-])=O.[N+:52]([C:55]1[CH:76]=[CH:75][C:58]2[NH:59][C:60]([NH:62][C:63]([C:65]3[N:66]=[CH:67][C:68]4[C:73]([CH:74]=3)=[CH:72][CH:71]=[CH:70][CH:69]=4)=[O:64])=[N:61][C:57]=2[CH:56]=1)([O-:54])=[O:53]>>[N+:52]([C:55]1[CH:76]=[CH:75][C:58]2[NH:59][C:60]([NH:62][C:63]([C:65]3[N:66]=[CH:67][C:68]4[C:73]([CH:74]=3)=[CH:72][CH:71]=[CH:70][CH:69]=4)=[O:64])=[N:61][C:57]=2[CH:56]=1)([O-:54])=[O:53].[NH2:52][C:55]1[CH:76]=[CH:75][C:58]2[NH:59][C:60]([NH:62][C:63]([C:65]3[N:66]=[CH:67][C:68]4[C:73]([CH:74]=3)=[CH:72][CH:71]=[CH:70][CH:69]=4)=[O:64])=[N:61][C:57]=2[CH:56]=1

Participants

6

Reactant 4

HCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 27367043-Isoquinolinecarboxylic acid hydrateHCID 178508200HCID 178508200, compoundHCID 178522497HCID 178522497, compound

Product 2

HCID 178507354HCID 178507354, compoundHCID 178522497HCID 178522497, compound

Procedure

Isoquinoline-3-carboxylic acid (5-nitro-1H-benzoimidazol-2-yl)-amide was synthesized from 3.5 g (20 mmol) of isoquinoline-3-carboxylic acid monohydrate, 7.6 g (20 mmol) of HBTU, and 3.56 g (20 mmol) of the above described 5-nitro-1H-benzoimidazol-2-ylamine as described in general procedure A. A 0.50 g (1.5 mmol) portion of this isoquinoline-3-carboxylic acid (5-nitro-1H-benzoimidazol-2-yl)-amide was subsequently hydrogenated according to general procedure C to produce isoquinoline-3-carboxylic acid (5-amino-1H-benzoimidazol-2-yl)-amide. LCMS: 304 (M+1)+.

Sources & evidence

ORD record
ord-bf8167e6ac68483cbf692f87836390b0
Source dataset
uspto-grants-2011_02
Patent number
US07893267B2

Reaction notes

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