Cyanoacetic acid → HCID 178511177, compound

HRID 1622407Notes

Reaction equation

[C:1]([CH2:3][C:4]([OH:6])=O)#[N:2].[N:7]1([CH2:13][C:14]2[CH:28]=[CH:27][C:17]3[NH:18][C:19]([C:21]4[C:25]([NH2:26])=[CH:24][NH:23][N:22]=4)=[N:20][C:16]=3[CH:15]=2)[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C>[C:1]([CH2:3][C:4]([NH:26][C:25]1[C:21]([C:19]2[NH:18][C:17]3[CH:27]=[CH:28][C:14]([CH2:13][N:7]4[CH2:8][CH2:9][O:10][CH2:11][CH2:12]4)=[CH:15][C:16]=3[N:20]=2)=[N:22][NH:23][CH:24]=1)=[O:6])#[N:2]

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of cyano-acetic acid (23 mg, 0.28 mmol), 3-(5-morpholin-4-ylmethyl-1H-benzimidazol-2-yl)-1H-pyrazol-4-ylamine (70%, 100 mg, 0.23 mmol), TBTU (89 mg, 0.28 mmol) and DMF (2 ml) was stirred at 25° C. overnight. The mixture was then evaporated in vacuo. Flash chromatography, eluting with DCM—6% MeOH/DCM afforded 2-cyano-N-[3-(5-morpholin-4-ylmethyl-1H-benzoimidazol-2-yl)-1H-pyrazol-4-yl]-acetamide as a yellow solid (65 mg, 77%). (LC/MS (acidic method/final compound): Rt 4.61, [M+H]+ 366).

Workup

customThe mixture was then evaporated in vacuo
washFlash chromatography, eluting with DCM—6% MeOH/DCM

Sources & evidence

ORD record: ord-884f829d7ec5470599c6e3da342c9531
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08778936B2

Reaction notes

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