Hydrochloric Acid → HCID 21471671, compound

HRID 2294947Notes

Reaction equation

C(OC([NH:8][C:9]1[N:14]=[CH:13][C:12]([C:15]([N:17]2[CH2:22][CH2:21][CH:20]([N:23]3[CH2:28][CH2:27][CH:26]([N:29]4[C:33]5[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=5[NH:31][C:30]4=[O:38])[CH2:25][CH2:24]3)[CH2:19][CH2:18]2)=[O:16])=[CH:11][N:10]=1)=O)(C)(C)C.[ClH:39]>C(OCC)(=O)C>[ClH:39].[ClH:39].[NH2:8][C:9]1[N:10]=[CH:11][C:12]([C:15]([N:17]2[CH2:18][CH2:19][CH:20]([N:23]3[CH2:28][CH2:27][CH:26]([N:29]4[C:33]5[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=5[NH:31][C:30]4=[O:38])[CH2:25][CH2:24]3)[CH2:21][CH2:22]2)=[O:16])=[CH:13][N:14]=1

Participants

Conditions

Temperature: -50 °C

Procedure

The 1,3-dihydro-1-{1-[1-(2-tert-butoxycarbonylamino-5-pyrimidinylcarbonyl)piperidin-4-yl]piperidin-4-yl}-2H-benzimidazol-2-one was dissolved in ethyl acetate, cooled to -50° C. and treated with a stream of HCl gas for 2 min. The reaction mixture was allowed to warm to room temperature and stir for several hours, and then concentrated to dryness under reduced pressure. The product 1,3-dihydro-1-{1-[1-(2-amino-5-pyrimidinecarbonyl)piperidin-4-yl]piperidin-4-yl}-2H-benzimidazol-2-one dihydrochloride salt, was obtained as white solid: Analysis calculated for C22H25N7O2.2 HCl.1.0 C7H8.3.0 H2O: C: 54.38, H: 6.77, N: 15.31; found C: 54.31, H: 6.48, N: 15.23.

Workup

temperatureto warm to room temperature
concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record: ord-a502673496e54607ad35e6d16061398d
Source dataset: uspto-grants-1997_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05691323

Reaction notes

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