Hydrochloric Acid → HCID 53374175, compound

HRID 869693Notes

Reaction equation

HRID 869693 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([N:6]=[C:7]([CH3:33])[C:8]([C:12]3[CH:32]=[C:15]4[N:16]=[C:17]([N:26]5[CH2:30][CH2:29][C@@H:28]([F:31])[CH2:27]5)[CH:18]=[C:19]([NH:20][CH2:21][C:22]([CH3:25])([OH:24])[CH3:23])[N:14]4[N:13]=3)=[N:9]2)=[CH:4][CH:3]=1.[ClH:34].O>C(O)C>[ClH:34].[F:1][C:2]1[CH:11]=[C:10]2[C:5]([N:6]=[C:7]([CH3:33])[C:8]([C:12]3[CH:32]=[C:15]4[N:16]=[C:17]([N:26]5[CH2:30][CH2:29][C@@H:28]([F:31])[CH2:27]5)[CH:18]=[C:19]([NH:20][CH2:21][C:22]([CH3:25])([OH:24])[CH3:23])[N:14]4[N:13]=3)=[N:9]2)=[CH:4][CH:3]=1.[F:1][C:2]1[CH:11]=[C:10]2[C:5]([N:6]=[C:7]([CH3:33])[C:8]([C:12]3[CH:32]=[C:15]4[N:16]=[C:17]([N:26]5[CH2:30][CH2:29][C@@H:28]([F:31])[CH2:27]5)[CH:18]=[C:19]([NH:20][CH2:21][C:22]([CH3:25])([OH:24])[CH3:23])[N:14]4[N:13]=3)=[N:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 53374175HCID 53374175, compound

Product 2

HCID 53374175HCID 53374175, compoundHCID 71074083HCID 71074083, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Conditions

Temperature
80 °C

Procedure

To a suspension of 1-({2-(7-fluoro-3-methylquinoxalin-2-yl)-5-[(3R)-3-fluoropyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-7-yl}amino)-2-methylpropan-2-ol (213 mg, 0.470 mmol) in ethanol (3.0 mL) was added 2N aqueous hydrochloric acid (0.282 mL), and the mixture was heated at 80° C., and then ethanol (2.0 mL) and water (0.2 mL) was added. The mixture was slowly cooled to ambient temperature and then ethanol (2.0 mL) was added. The resulting precipitate was collected, and washed with diethyl ether to give 1-({2-(7-fluoro-3-methylquinoxalin-2-yl)-5-[(3R)-3-fluoropyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-7-yl}amino)-2-methylpropan-2-ol hydrochloride (the compound of Example 1.006 listed in the Table of Examples as described hereinafter). 1H-NMR (400 MHz, DMSO-d6): δ 1.24 (6H, s), 2.25-2.43 (2H, m), 3.10 (3H, s), 3.62-3.70 (2H, m), 3.80-4.01 (4H, m), 5.52-5.63 (1H, m), 5.71 (1H, s), 6.94 (1H, s), 7.81 (1H, ddd, J=9.1, 8.8, 2.7 Hz), 7.95 (1H, dd, J=9.6, 2.9 Hz), 7.99 (1H, br), 8.14 (1H, dd, J=9.1, 5.9 Hz).

Workup

  1. temperatureThe mixture was slowly cooled to ambient temperature
  2. customThe resulting precipitate was collected
  3. washwashed with diethyl ether

Sources & evidence

ORD record
ord-f090ab8d904f43c5855d047adcfb47c6
Source dataset
uspto-grants-2015_03
Patent number
US08969376B2

Reaction notes

Loading…