Isoquinoline-3-carboxylic acid → HCID 58724415, compound

HRID 1845046Notes

Reaction equation

HRID 1845046 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[N:49]=[C:48]([NH2:51])[NH:47][C:46]=2[CH:45]=[C:44]([CH2:52][CH2:53][CH3:54])[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]=[C:44]([CH2:52][CH2:53][CH3:54])[CH:43]=1)=[O:41]

Participants

4

Reactant 3

HCID 124656Isoquinoline-3-carboxylic acidHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66940377HCID 66940377, compound

Product 1

HCID 58724415HCID 58724415, compoundYield 75%

Procedure

0.4 g (75%) of 2-[(isoquinoline-3-carbonyl)-amino]-6-propyl-1H-benzoimidazole-4-carboxylic acid methyl ester was synthesized from 0.25 g (1.4 mmol) of isoquinoline-3-carboxylic acid, 0.6 g (1.6 mmol) of HBTU, and 0.3 g (1.3 mmol) of the above synthesized 2-Amino-6-propyl-1H-benzoimidazole-4-carboxylic acid methyl ester as described in general procedure A. LCMS: 389 (M+1)+.

Sources & evidence

ORD record
ord-8bdaae57b606449f8c271917f1f82a44
Source dataset
uspto-grants-2015_02
Patent number
US08946259B2

Reaction notes

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