Diisopropylethylamine → HCID 58026467, compound

HRID 1367916Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:10]=[N:11][CH:12]=[C:13]([CH:17]=1)[C:14]([OH:16])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[NH:51]1[CH:55]=[CH:54][N:53]=[C:52]1[NH:56][C:57]([C:59]1[C:67]2[NH:66][C:65]([NH2:68])=[N:64][C:63]=2[CH:62]=[CH:61][CH:60]=1)=[O:58]>O.CN(C=O)C>[NH:53]1[CH:54]=[CH:55][N:51]=[C:52]1[NH:56][C:57]([C:59]1[C:67]2[N:66]=[C:65]([NH:68][C:14]([C:13]3[CH:12]=[N:11][CH:10]=[C:9]([O:8][CH2:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)[CH:17]=3)=[O:16])[NH:64][C:63]=2[CH:62]=[CH:61][CH:60]=1)=[O:58]

Participants

Conditions

Temperature: 80 °C

Procedure

0.07 g (0.30 mmol) of 5-benzyloxy-nicotinic acid and 0.12 g (0.32 mmol) of HBTU were combined in a flask charged with 2 mL DMF and 0.25 mL of DIEA. This reaction mixture was then treated with 0.05 g (0.20 mmol) of 2-Amino-3H-benzoimidazole-4-carboxylic acid (1H-imidazol-2-yl)-amide (Intermediate B) and stirred at 80° C. for 1 h. The reaction mixture was diluted with water, and the resultant solid precipitate was filtered and washed with saturated NaHCO3. The solid was dissolved with MeOH, evaporated onto silica gel and isolated by flash column chromatography (500 mL DCM/20 mL NH3/MeOH) to yield 10 mg (10%) of 2-[(5-benzyloxy-pyridine-3-carbonyl)-amino]-1H-benzoimidazole-4-carboxylic acid (1H-imidazol-2-yl)-amide. LCMS: 455.0 (M+1)+.

Workup

filtrationthe resultant solid precipitate was filtered
washwashed with saturated NaHCO3
dissolutionThe solid was dissolved with MeOH
customevaporated onto silica gel
customisolated by flash column chromatography (500 mL DCM/20 mL NH3/MeOH)

Sources & evidence

ORD record: ord-80a1bc1f3a0341958b20b6613699e7ee
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07893267B2

Reaction notes

Loading…