Isoquinoline-3-carboxylic acid → HCID 66940467, compound

HRID 1844956Notes

Reaction equation

[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([C:11]([OH:13])=O)[N:2]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:38][O:39][C:40]([C:42]1[C:50]2[NH:49][C:48]([NH2:51])=[N:47][C:46]=2[CH:45]=[CH:44][CH:43]=1)=[O:41]>>[CH3:38][O:39][C:40]([C:42]1[C:50]2[N:49]=[C:48]([NH:51][C:11]([C:3]3[N:2]=[CH:1][C:10]4[C:5]([CH:4]=3)=[CH:6][CH:7]=[CH:8][CH:9]=4)=[O:13])[NH:47][C:46]=2[CH:45]=[CH:44][CH:43]=1)=[O:41]

Participants

Reactant 3

HCID 124656Isoquinoline-3-carboxylic acid

HCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

HCID 178497585HCID 178497585, compound

Product 1

HCID 66940467HCID 66940467, compoundYield 75.5%

Procedure

2.6 g (75%) of the 2-[(isoquinoline-3-carbonyl)-amino]-1H-benzoimidazole-4-carboxylic acid methyl ester was synthesized from isoquinoline-3-carboxylic acid (1.7 g, 10 mmol), HBTU (4.6 g, 12 mmol), and the above synthesized 2-amino-3H-benzoimidazole-4-carboxylic acid methyl ester (1.9 g, 10 mml) as described in general procedure A. This ester was then hydrolyzed according to general procedure B to give 2.2 g (88%) of acid. LCMS: 333 (M+1)+.

Sources & evidence

ORD record: ord-c5dff030b5594b98a64ab4cf46cbda63
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946259B2

Reaction notes

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