Hydrochloric Acid → HCID 67520783, compound

HRID 1926244Notes

Reaction equation

HRID 1926244 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[CH:18]=[C:17]([C:19]3[CH:20]=[N:21][C:22]([NH2:37])=[C:23]([C:25]4[N:26]=[CH:27][C:28]5[C:33]([CH:34]=4)=[C:32]([CH3:35])[CH:31]=[CH:30][C:29]=5[F:36])[CH:24]=3)[CH:16]=[N:15]2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(Cl)[Cl:39].[ClH:41].CCOCC>>[ClH:39].[ClH:41].[ClH:39].[F:36][C:29]1[CH:30]=[CH:31][C:32]([CH3:35])=[C:33]2[C:28]=1[CH:27]=[N:26][C:25]([C:23]1[C:22]([NH2:37])=[N:21][CH:20]=[C:19]([C:17]3[CH:16]=[N:15][N:14]([CH:11]4[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]4)[CH:18]=3)[CH:24]=1)=[CH:34]2

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 6344DichloromethaneHCID 67520948HCID 67520948, compound

Product 1

HCID 67520783HCID 67520783, compound

Procedure

To a solution of 4-{4-[6-amino-5-(8-fluoro-5-methylisoquinolin-3-yl)-pyridin-3-yl]-pyrazol-1-yl}-piperidine-1-carboxylic acid tert-butyl ester (11.5 mg, 0.0229 mmol) in DCM (0.60 mL, 9.4 mmol) was added 1.0 M of HCl in Et2O (0.80 mL, 0.80 mmol), and the mixture was stirred at ambient temperature for 2 h. Almost immediately a pale yellow solid precipitated. The solvents were evaporated, and the residue was transferred into a vial and dried in vacuo overnight, yielding the title compound as yellow solid. 1H NMR (400 MHz, DMSO-d6): δ=14.6 (very brs, 1H), 9.59 (d, J=0.8 Hz, 1H), 9.19-9.09 (brm, 1H), 9.02-8.91 (brm, 1H), 8.88 (d, J=2.4 Hz, 1H), 8.56 (brs, 1H), 8.54 (s, 1H), 8.48 (s, 1H), 8.47 (d, J=2.4 Hz, 1H), 8.15 (s, 1H), 7.73 (ddd, J=0.8, 6.4, 8.0 Hz, 1H), 7.51 (dd, J=8.0, 10.2 Hz, 1H), 4.59-4.50 (mc, 1H), 3.40 (brd, J=12.2 Hz, 2H), 3.11 (brq, J=11.4 Hz, 2H), 2.76 (s, 3H), 2.30-2.12 (m, 4H). MS(ES+): m/z=403.16 (23) [MH+], 320.12 (100) [MH+-piperidine]. HPLC: tR=1.89 min (polar—5 min, ZQ2).

Workup

  1. customAlmost immediately a pale yellow solid precipitated
  2. customThe solvents were evaporated
  3. customdried in vacuo overnight

Sources & evidence

ORD record
ord-020e8785a08e4ca0a0453714587369fc
Source dataset
uspto-grants-2012_05
Patent number
US08178668B2

Reaction notes

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