Hydrochloric Acid → HCID 67521037, compound

HRID 1926224Notes

Reaction equation

HRID 1926224 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]=[C:27]([CH3:35])[C:28]5[C:33]([CH:34]=4)=[CH:32][CH:31]=[CH:30][CH:29]=5)[CH:24]=3)[CH:16]=[N:15]2)[CH2:10][CH2:9]1)=O)(C)(C)C.O1CCOCC1.[ClH:43]>>[ClH:43].[ClH:43].[ClH:43].[CH3:35][C:27]1[C:28]2[C:33](=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:34]=[C:25]([C:23]2[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]=2)[N:26]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-Dioxane2×HCID 675216054-{4-[6-Amino-5-(1-methylisoquinolin-3-yl)-pyridin-3-yl]-pyrazol-1-yl}-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 67521037HCID 67521037, compound

Procedure

To a solution of 4-{4-[6-Amino-5-(1-methylisoquinolin-3-yl)-pyridin-3-yl]-pyrazol-1-yl}-piperidine-1-carboxylic acid tert-butyl ester (36.8 mg, 0.0759 mmol) in 1,4-dioxane (1.0 mL, 13 mmol) was added 4.0 M of HCl in 1,4-dioxane (1.0 mL, 4.0 mmol), and the mixture was stirred at ambient temperature for 1.5 h. Almost immediately a pale yellow solid precipitated. The solid was filtered off, washed with MTBE, and dried in vacuo, giving the title compound as pale yellow solid. 1H NMR (400 MHz, DMSO-d6): δ=14.7 (very brs, 1H), 9.33-9.23 (brm, 1H), 9.21-9.08 (brm, 1H), 8.82 (d, J=1.8 Hz, 1H), 8.8 (very brs, 2H), 8.59 (s, 1H), 8.50 (s, 1H), 8.48 (d, J=1.8 Hz, 1H), 8.38 (d, J=8.4 Hz, 1H), 8.14 (s, 1H), 8.13 (d, J=8.0 Hz, 1H), 7.95 (dd, J=7.2, 7.2 Hz, 1H), 7.84 (dd, J=7.8, 7.8 Hz, 1H), 4.58-4.49 (mc, 1H), 3.39 (brd, J=12.6 Hz, 2H), 3.11 (brq, J=11.4 Hz, 2H), 3.07 (s, 3H), 2.30-2.13 (m, 4H). MS(ES+): m/z=385.15 (53) [MH+], 302.12 (100) [MH+-piperidine]. HPLC: tR=1.88 min (polar—5 min, ZQ3).

Workup

  1. customAlmost immediately a pale yellow solid precipitated
  2. filtrationThe solid was filtered off
  3. washwashed with MTBE
  4. customdried in vacuo

Sources & evidence

ORD record
ord-11f78c93855f4651aaa0791ad417e4d8
Source dataset
uspto-grants-2012_05
Patent number
US08178668B2

Reaction notes

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