Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → HCID 178497383, compound

HRID 1367860Notes

Reaction equation

HRID 1367860 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.COC(C1C=CC2NC(N)=NC=2C=1)=O.[CH3:53][O:54][C:55]([C:57]1[CH:78]=[CH:77][C:60]2[NH:61][C:62]([NH:64][C:65]([C:67]3[N:68]=[CH:69][C:70]4[C:75]([CH:76]=3)=[CH:74][CH:73]=[CH:72][CH:71]=4)=[O:66])=[N:63][C:59]=2[CH:58]=1)=[O:56]>>[CH3:53][O:54][C:55]([C:57]1[CH:78]=[CH:77][C:60]2[NH:61][C:62]([NH:64][C:65]([C:67]3[N:68]=[CH:69][C:70]4[C:75]([CH:76]=3)=[CH:74][CH:73]=[CH:72][CH:71]=4)=[O:66])=[N:63][C:59]=2[CH:58]=1)=[O:56].[CH:69]1[C:70]2[C:75](=[CH:74][CH:73]=[CH:72][CH:71]=2)[CH:76]=[C:67]([C:65]([NH:64][C:62]2[NH:61][C:60]3[CH:77]=[CH:78][C:57]([C:55]([OH:56])=[O:54])=[CH:58][C:59]=3[N:63]=2)=[O:66])[N:68]=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 178497383HCID 178497383, compoundHCID 178497384HCID 178497384, compound

Product 2

HCID 178497383HCID 178497383, compoundHCID 178524177HCID 178524177, compound

Procedure

2-[(Isoquinoline-3-carbonyl)-amino]-1H-benzoimidazole-5-carboxylic acid methyl ester was prepared from 1.9 g (10 mmol) of isoquinoline-3-carboxylic acid monohydrate, 4.6 g (12 mmol) of HBTU, and 1.9 g, (10 mmol) of 2-amino-1H-benzoimidazole-5-carboxylic acid methyl ester as described in general procedure A. A 0.35 g (1.0 mmol) portion of 2-[(isoquinoline-3-carbonyl)-amino]-1H-benzoimidazole-5-carboxylic acid methyl ester was subsequently hydrolyzed according to general procedure B to give 2-[(isoquinoline-3-carbonyl)-amino]-1H-benzoimidazole-5-carboxylic acid as a light yellow solid, which was used in the final coupling step without further purification.

Sources & evidence

ORD record
ord-b43d99d2c7da46ab8c94b31bb4471051
Source dataset
uspto-grants-2011_02
Patent number
US07893267B2

Reaction notes

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