Bis(2-amino-1H-imidazole) sulphate → HCID 178522544, compound

HRID 1910116Notes

Reaction equation

[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([NH:11][C:12]2[NH:13][C:14]3[C:20]([C:21](O)=[O:22])=[CH:19][CH:18]=[CH:17][C:15]=3[N:16]=2)[N:2]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.S(O)(O)(=O)=O.[NH2:53][C:54]1[NH:55][CH:56]=[CH:57][N:58]=1>>[NH:55]1[CH:56]=[CH:57][N:58]=[C:54]1[NH:53][C:21]([C:20]1[C:14]2[NH:13][C:12]([NH: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)=[N:16][C:15]=2[CH:17]=[CH:18][CH:19]=1)=[O:22]

Participants

Reactant 3

HCID 135136Bis(2-amino-1H-imidazole) sulphate

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

HCID 178524250HCID 178524250, compound

Product 1

HCID 178522544HCID 178522544, compoundYield 16.4%

Procedure

100 mg (0.33 mmol) of the above carboxylic acid was reacted with 200 mg (0.53 mmol) of HBTU and 200 mg (1.2 mmol) of 2-aminoimidazole sulfate according to the general procedure A. The crude product was purified by flash column chromatography (EtOAc then EtOAc/MeOH=10:1) to give 2-(isoquinolin-3-ylamino)-3H-benzoimidazole-4-carboxylic acid (1H-imidazol-2-yl)-amide (20 mg, 15%). LCMS: 370 (M+1)+. 1H NMR (DMSO-d6, 400 MHz): δ 6.82 (s, 1H), 6.89 (s, 1H), 7.20 (dd, 1H), 7.47 (dd, 1H), 7.71 (m, 2H), 7.84 (dd, 1H), 8.04 (s, 1H), 8.08 (d, 1H), 8.18 (d, 1H), 9.21 (s, 1H), 11.14 (s, 1H), 11.84 (s, 1H), 12.11 (s, 1H), 12.60 (s, 1H) ppm.

Workup

customThe crude product was purified by flash column chromatography (EtOAc

Sources & evidence

ORD record: ord-1f20e48da7a240d08488be0d0388b1eb
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08598353B2

Reaction notes

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