Hydrochloric Acid → HCID 67521376, compound

HRID 1926232Notes

Reaction equation

HRID 1926232 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[Cl:35])[CH:24]=3)[CH:16]=[N:15]2)[CH2:10][CH2:9]1)=O)(C)(C)C.O1CCOCC1.[ClH:43]>>[ClH:35].[ClH:43].[ClH:35].[Cl: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[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]4)[CH:18]=3)[CH:24]=1)=[CH:34]2

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 67520796HCID 67520796, compound

Product 1

HCID 67521376HCID 67521376, compound

Procedure

To a solution of 4-{4-[6-amino-5-(8-chloroisoquinolin-3-yl)-pyridin-3-yl]-pyrazol-1-yl}-piperidine-1-carboxylic acid tert-butyl ester (64.2 mg, 0.127 mmol) in 1,4-dioxane (1.5 mL, 19 mmol) was added HCl (4.0 M in 1,4-dioxane; 1.2 mL, 4.8 mmol), and the mixture was stirred at ambient temperature for 70 min. Almost immediately an off-white solid precipitated. The solid was filtered off, washed with MTBE, and dried in vacuo overnight to give the title compound as yellow solid. It appeared to be slightly hygroscopic during the filtration; however, after the washing and initial drying it appeared to be non-hygroscopic. 1H NMR (400 MHz, DMSO-d6): δ=14.7 (very brs, 1H), 9.68 (s, 1H), 9.23-9.14 (brm, 1H), 9.12-8.99 (brm, 1H), 8.89 (d, J=2.0 Hz, 1H), 8.82 (s, 1H), 8.76 (brs, 2H), 8.52 (s, 1H), 8.49 (d, J=2.0 Hz, 1H), 8.16 (s, 1H), 8.12 (d, J=8.0 Hz, 1H), 7.95 (dd, J=1.2, 7.6 Hz, 1H), 7.90 (t, J=7.8 Hz, 1H), 4.58-4.49 (mc, 1H), 3.40 (brd, J=12.0 Hz, 2H), 3.07 (brq, J=11.2 Hz, 2H), 2.30-2.12 (m, 4H). MS(ES+): m/z=405.13/407.13 (88/60) [MH+], 322.07/324.05 (90/64) [MH+-piperidine]. HPLC: tR=1.98 min (polar—5 min, ZQ3). UV: λmax=210, 244, 352 nm.

Workup

  1. customAlmost immediately an off-white solid precipitated
  2. filtrationThe solid was filtered off
  3. washwashed with MTBE
  4. customdried in vacuo overnight

Sources & evidence

ORD record
ord-79257743e1524a259c7b1162e4bb4117
Source dataset
uspto-grants-2012_05
Patent number
US08178668B2

Reaction notes

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