Hydrochloric Acid → HCID 67521046, compound

HRID 1926327Notes

Reaction equation

HRID 1926327 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]([NH2:35])=[C:23]([C:25]4[O:26][C:27]5[CH:34]=[CH:33][CH:32]=[CH:31][C:28]=5[C:29]=4[Cl:30])[CH:24]=3)[CH:16]=[N:15]2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(Cl)[Cl:37].Cl.CCOCC>>[ClH:30].[ClH:37].[Cl:30][C:29]1[C:28]2[CH:31]=[CH:32][CH:33]=[CH:34][C:27]=2[O:26][C:25]=1[C:23]1[C:22]([NH2:35])=[N:21][CH:20]=[C:19]([C:17]2[CH:16]=[N:15][N:14]([CH:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)[CH:18]=2)[CH:24]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 6344DichloromethaneHCID 67520782HCID 67520782, compound

Product 1

HCID 67521046HCID 67521046, compound

Procedure

To a solution of 4-{4-[6-Amino-5-(3-chlorobenzofuran-2-yl)-pyridin-3-yl]-pyrazol-1-yl}-piperidine-1-carboxylic acid tert-butyl ester (78.0 mg, 0.158 mmol) in DCM (2.5 mL, 39 mmol) was added 1.0 M of HCl in Et2O (1.5 mL; 1.5 mmol), and the mixture was stirred at ambient temperature for 8.5 h. The solid formed was filtered off, washed with DCM, and dried in vacuo overnight, yielding the title compound as yellow solid. 1H NMR (400 MHz, DMSO-d6): δ=9.20-9.09 (brm, 1H), 9.02-8.91 (brm, 1H), 8.57 (d, J=2.0 Hz, 1H), 8.52 (d, J=2.0 Hz, 1H), 8.39 (s, 1H), 8.05 (s, 1H), 7.96 (very brs, 2H), 7.76 (d, J=8.4 Hz, 1H), 7.74 (dd, J=8.4, 0.8 Hz, 1H), 7.55 (ddd, J=1.2, 7.2, 8.4 Hz, 1H), 7.48 (ddd, J=0.8, 7.2, 8.4 Hz, 1H), 4.55-4.46 (mc, 1H), 3.38 (brd, J=12.8 Hz, 2H), 3.08 (q, J=12.2 Hz, 2H), 2.26-2.08 (m, 4H). MS(ES+): m/z=394.10/396.09 (65/21) [MH+], 311.04/313.07 (100/34) [MH+-piperidine]. HPLC: tR=2.28 min (polar—5 min, ZQ3).

Workup

  1. customThe solid formed
  2. filtrationwas filtered off
  3. washwashed with DCM
  4. customdried in vacuo overnight

Sources & evidence

ORD record
ord-74fd985db9c64f7f89232cc51b2db76e
Source dataset
uspto-grants-2012_05
Patent number
US08178668B2

Reaction notes

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