Water → HCID 178511940, compound

HRID 983797Notes

Reaction equation

CCN(C(C)C)C(C)C.[OH:10][C:11]1[C:16]([C:17]2[NH:25][C:20]3[CH2:21][NH:22][CH2:23][CH2:24][C:19]=3[N:18]=2)=[CH:15][CH:14]=[CH:13][C:12]=1[C:26]1[NH:30][C:29]2[CH:31]=[CH:32][C:33]([C:35]([NH2:37])=[NH:36])=[CH:34][C:28]=2[N:27]=1.Cl.[N:39]1([C:44](N)=[NH:45])C=CC=N1.O>CN(C=O)C.C(OCC)C>[C:35]([C:33]1[CH:32]=[CH:31][C:29]2[NH:30][C:26]([C:12]3[C:11]([OH:10])=[C:16]([C:17]4[NH:25][C:20]5[CH2:21][N:22]([C:44]([NH2:45])=[NH:39])[CH2:23][CH2:24][C:19]=5[N:18]=4)[CH:15]=[CH:14][CH:13]=3)=[N:27][C:28]=2[CH:34]=1)(=[NH:37])[NH2:36]

Participants

Conditions

Temperature: 80 °C

Procedure

Hunig's base (0.042 mL, 0.24 mmol) was added to a suspension of 2-[2-Hydroxy-3-(4,5,6,7-tetrahydro-3H-imidazo[4,5-c]pyridin-2-yl)-phenyl]-1H-benzoimidazole-5-carboxamidine 75 (19 mg, 0.04 mmol) and 1H-pyrazole-1-carboxamidine hydrochloride (12 mg, 0.082 mmol) in anhydrous DMF and the mixture was stirred for 12-18 h at 80° C. The mixture was poured into water (15 mL)/diethyl ether (15 mL). The aqueous layer was washed with diethyl ether (3×10 mL) and concentrated to dryness. HPLC purification (2-50% acetonitrile/60 minutes) afforded 2-[3-(5-Carbamimidoyl-1H-benzoimidazol-2-yl)-2-hydroxy-phenyl]-3,4,6,7-tetrahydro-imidazo[4,5-c]pyridine-5-carboxamidine 76 as a lyophilized yellow light powder (15.5 mg, 75% yield) (Example 298, Table 2a).

Workup

washThe aqueous layer was washed with diethyl ether (3×10 mL)
concentrationconcentrated to dryness
customHPLC purification (2-50% acetonitrile/60 minutes)

Sources & evidence

ORD record: ord-696f5e210a7d482dbe5dbfd79c72e6cd
Source dataset: uspto-grants-2005_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06867200B1

Reaction notes

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