Hydrochloric Acid → HCID 67521942, compound

HRID 1926240Notes

Reaction equation

HRID 1926240 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]([NH2:36])=[C:23]([C:25]4[N:26]=[CH:27][C:28]5[C:33]([CH:34]=4)=[CH:32][CH:31]=[CH:30][C:29]=5[CH3:35])[CH:24]=3)[CH:16]=[N:15]2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(Cl)[Cl:38].[ClH:40].CCOCC>>[ClH:38].[ClH:40].[ClH:38].[CH3:35][C:29]1[CH:30]=[CH:31][CH:32]=[C:33]2[C:28]=1[CH:27]=[N:26][C:25]([C:23]1[C:22]([NH2:36])=[N:21][CH:20]=[C:19]([C:17]3[CH:16]=[N:15][N:14]([CH:11]4[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]4)[CH:18]=3)[CH:24]=1)=[CH:34]2

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 6344DichloromethaneHCID 67521024HCID 67521024, compound

Product 1

HCID 67521942HCID 67521942, compound

Procedure

To a solution of 4-{4-[6-amino-5-(8-methylisoquinolin-3-yl)-pyridin-3-yl]-pyrazol-1-yl}-piperidine-1-carboxylic acid tert-butyl ester (11.0 mg, 0.0227 mmol) in DCM (0.40 mL, 6.2 mmol) was added 1.0 M of HCl in Et2O (0.60 mL, 0.60 mmol), and the mixture was stirred at ambient temperature for 2 h. Almost immediately an off-white solid precipitated. The solvents were evaporated, and the residue was suspended in Et2O, filtered off, and dried in vacuo overnight, yielding the title compound as yellow solid. It appeared to be hygroscopic during the filtration; however, after the washing and initial drying it appeared to be non-hygroscopic. 1H NMR (400 MHz, DMSO-d6): δ=14.6 (very brs, 1H), 9.60 (s, 1H), 9.18-9.07 (brm, 1H), 9.05-8.92 (brm, 1H), 8.88 (d, J=2.0 Hz, 1H, 8.86 (brs, 1H), 8.73 (s, 1H), 8.51 (s, 1H), 8.45 (d, J=2.0 Hz, 1H), 8.16 (d, J=0.4 Hz, 1H), 7.95 (d, J=8.4 Hz, 1H), 7.81 (dd, J=8.4, 6.8 Hz, 1H), 7.61 (d, J=6.8 Hz, 1H), 4.58-4.49 (m, 1H), 3.40 (brd, J=12.4 Hz, 2H), 3.12 (brq, J=12.2 Hz, 2H), 2.83 (s, 3H), 2.30-2.12 (m, 4H). MS(ES+): m/z=385.21 (43) [MH+], 302.15 (100) [MH+-piperidine]. HPLC: tR=1.80 min (polar—5 min, ZQ2).

Workup

  1. customAlmost immediately an off-white solid precipitated
  2. customThe solvents were evaporated
  3. filtrationfiltered off
  4. customdried in vacuo overnight

Sources & evidence

ORD record
ord-9701a625fc8a4da885309c640359e806
Source dataset
uspto-grants-2012_05
Patent number
US08178668B2

Reaction notes

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