Hydrochloric Acid → HCID 71164946, compound

HRID 2173108Notes

Reaction equation

HRID 2173108 reaction equation
C(OC([NH:8][C@H:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]1[NH:15][C:16]1[N:21]=[C:20]([C:22]2[CH:23]=[N:24][N:25]3[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][C:26]=23)[C:19]2[C:32](=[O:42])[N:33](C(OC(C)(C)C)=O)[CH2:34][C:18]=2[C:17]=1[F:43])=O)(C)(C)C.[ClH:44]>C(O)(C)C>[ClH:44].[NH2:8][C@H:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]1[NH:15][C:16]1[N:21]=[C:20]([C:22]2[CH:23]=[N:24][N:25]3[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][C:26]=23)[C:19]2[C:32](=[O:42])[NH:33][CH2:34][C:18]=2[C:17]=1[F:43]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 71164906HCID 71164906, compound

Product 2

HCID 313Hydrochloric AcidHCID 71164946HCID 71164946, compoundYield 102.8%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of tert-butyl 6-(((1R,2S)-2-((tert-butoxycarbonyl)amino)cyclo-hexyl)amino)-7-fluoro-4-(5-methylpyrazolo[1,5-a]pyridin-3-yl)-3-oxo-1H-pyrrolo[3,4-c]pyridine-2(3H)-carboxylate (110 mg, 0.185 mmol) in isopropanol (10 mL) at 65° C. was added concentrated HCl (0.268 mL, 3.21 mmol) dropwise. The reaction mixture was stirred at 65° C. overnight and then slowly cooled. The solids were filtered and dried to give an HCl salt of the title compound as a pale yellow solid (75 mg, 94%). 1H NMR (500 MHz, DMSO-d6) δ ppm 1.49 (br s, 1H) 1.61-1.82 (m, 1H) 1.96 (d, J=8.79 Hz, 1H) 2.44 (s, 3H), 4.33-4.45 (m, 2H) 6.81 (d, J=6.35 Hz, 1H) 6.88 (dd, J=7.02, 1.83 Hz, 1H) 7.90 (br s, 2H) 8.20 (s, 1H) 8.37 (s, 1H) 8.66 (d, J=7.02 Hz, 1H) 9.33 (s, 1H). [M+H] calc'd for C21H23FN6O, 395. found, 395.

Workup

  1. temperatureslowly cooled
  2. filtrationThe solids were filtered
  3. customdried

Sources & evidence

ORD record
ord-81695e6dcf974f418535b8f2f83955da
Source dataset
uspto-grants-2015_06
Patent number
US09056873B2

Reaction notes

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