Hydrochloric Acid → HCID 86607240, compound

HRID 969886Notes

Reaction equation

HRID 969886 reaction equation
[ClH:1].Cl.CN1C2CCCC1CC([NH:13][C:14]([C:16]1[CH:17]=[C:18]([NH2:31])[CH:19]=[C:20]3[O:24][C:23]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[N:22][C:21]=13)=[O:15])C2.Cl>CO.C(OCC)C>[ClH:1].[ClH:1].[NH2:31][C:18]1[CH:19]=[C:20]2[O:24][C:23]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)=[N:22][C:21]2=[C:16]([C:14]([NH2:13])=[O:15])[CH:17]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 68458647HCID 68458647, compound

Product 1

HCID 86607240HCID 86607240, compoundYield 106.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of the amide from Step B (120 mg, 0.31 mmol) in methanol (1.0 mL) was added a solution of HCl in diethyl ether (1 N, 0.93 mL, 0.93 mmol) at room temperature slowly. The reaction mixture was diluted with diethyl ether. The resulting solid was filtered and washed with diethyl ether to afford N-(9-methyl-9-azabicyclo[3.3.1]non-6-amino-2-phenylbenzoxazole-4-carboxamide dihydrochloride (54 mg, 38%) as a yellow solid: 1H NMR (500 MHz, DMSO-d6) δ 10.48 (br s, 0.4H), 9.69 (br s, 0.6H), 9.16 (d, J=5.8 Hz, 0.6H), 8.88 (d, J=6.9 Hz, 0.4H), 8.23-8.15 (m, 2H), 7.70-7.60 (m, 3H), 7.55-7.50 (m, 1H), 7.36 (s, 1H), 4.90-4.35 (m, 4H), 3.70-3.65 (m, 1.4H), 3.60-3.55 (m, 0.6H), 2.90-2.80 (m, 4H), 2.75-2.60 (m, 2H), 2.40-2.10 (m, 3H), 1.95-1.82 (m, 2H), 1.60-1.50 (m, 2H); MS (ESI+) m/z 391 (M+H); HPLC>99% (AUC), tR=11.49 min.

Workup

  1. filtrationThe resulting solid was filtered
  2. washwashed with diethyl ether

Sources & evidence

ORD record
ord-e55bea077665441f848e98a44ac40adb
Source dataset
uspto-grants-2007_12
Patent number
US07307094B2

Reaction notes

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