Hydrochloric Acid → HCID 71143898, compound

HRID 2173106Notes

Reaction equation

HRID 2173106 reaction equation
C(OC([NH:8][C@@H:9]1[C@H:14]([NH:15][C:16]2[N:21]=[C:20]([C:22]3[CH:23]=[N:24][N:25]4[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][C:26]=34)[C:19]3[C:32](=[O:42])[N:33](C(OC(C)(C)C)=O)[CH2:34][C:18]=3[C:17]=2[F:43])[CH2:13][CH2:12][O:11][CH2:10]1)=O)(C)(C)C.[ClH:44]>C(O)(C)C>[ClH:44].[NH2:8][C@@H:9]1[C@H:14]([NH:15][C:16]2[N:21]=[C:20]([C:22]3[CH:23]=[N:24][N:25]4[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][C:26]=34)[C:19]3[C:32](=[O:42])[NH:33][CH2:34][C:18]=3[C:17]=2[F:43])[CH2:13][CH2:12][O:11][CH2:10]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 71143864HCID 71143864, compound

Product 2

HCID 313Hydrochloric AcidHCID 71143898HCID 71143898, compoundYield 100.9%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of tert-butyl 6-(((3R,4R)-3-((tert-butoxycarbonyl)amino)tetrahydro-2H-pyran-4-yl)amino)-7-fluoro-4-(5-methylpyrazolo[1,5-a]pyridin-3-yl)-3-oxo-1H-pyrrolo[3,4-c]pyridine-2(3H)-carboxylate (45 mg, 0.075 mmol) in isopropanol (5 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 (30 mg, 92%). 1H NMR (500 MHz, DMSO-d6) δ ppm 1.84 (d, J=9.88 Hz, 1H), 2.08-2.22 (m, 1H), 2.46 (s, 3H), 3.55-3.67 (m, 2H), 3.94-4.09 (m, 2H), 4.35-4.47 (m, 2H), 6.88 (dd, J=7.08, 1.83 Hz, 1H), 7.12 (d, J=5.98 Hz, 1H), 8.03 (d, J=3.97 Hz, 2H), 8.15 (s, 1H), 8.39 (s, 1H), 8.66 (d, J=7.08 Hz, 1H), 9.24 (s, 1H). [M+H] calc'd for C20H21FN6O2, 397. found, 397.

Workup

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

Sources & evidence

ORD record
ord-a538cd1ea9d04e549718f19b297997a7
Source dataset
uspto-grants-2015_06
Patent number
US09056873B2

Reaction notes

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