Hydrochloric Acid → HCID 178508054, compound

HRID 1946274Notes

Reaction equation

C(OC(=O)[NH:7][C:8]1[C:9]([C:13](=O)[NH:14][C:15]2[CH:20]=[CH:19][C:18]([CH2:21][N:22]3[CH2:27][CH2:26][O:25][CH2:24][CH2:23]3)=[CH:17][C:16]=2[NH2:28])=[N:10][NH:11][CH:12]=1)(C)(C)C.Cl.C([O-])([O-])=O.[Na+].[Na+]>CCOCC>[N:22]1([CH2:21][C:18]2[CH:19]=[CH:20][C:15]3[NH:14][C:13]([C:9]4[C:8]([NH2:7])=[CH:12][NH:11][N:10]=4)=[N:28][C:16]=3[CH:17]=2)[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1

Participants

Conditions

Temperature: 85 °C

Procedure

A mixture of [3-(2-amino-4-morpholin-4-ylmethyl-phenylcarbamoyl)-1H-pyrazol-4-yl]-carbamic acid tert-butyl ester (12.0 g, 28.8 mmol) and 2M aqueous HCl solution (50 μL) was heated at 85° C. for 14 h, then allowed to cool to ambient temperature. Solid Na2CO3 was carefully added until mixture was pH˜8.5 and solution was saturated. A dark coloured gummy liquid was formed. The mixture was allowed to settle and the solvent decanted. To the remaining residue was added EtOH (60 mL), the mixture heated at reflux for 1 h and then hot filtered, washing with EtOH (2×20 mL), to remove inorganic residues. The filtrate was reduced in vacuo to give a glassy solid which was then stirred in Et2O (60 mL) for 1 h and the resultant purple coloured powder collected by filtration and dried in vacuo to give 3-(5-morpholin-4-ylmethyl-1H-benzoimidazol-2-yl)-1H-pyrazol-4-ylamine (6.8 g, 80%, ˜90% purity).

Workup

temperatureto cool to ambient temperature
customA dark coloured gummy liquid was formed
customthe solvent decanted
additionTo the remaining residue was added EtOH (60 mL)
temperaturethe mixture heated
temperatureat reflux for 1 h
washhot filtered, washing with EtOH (2×20 mL)
customto remove inorganic residues
customto give a glassy solid which
filtrationcollected by filtration
customdried in vacuo

Sources & evidence

ORD record: ord-51294c3b8218450a891f22546cca9550
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399442B2

Reaction notes

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