Sodium Carbonate → HCID 67520735, compound

HRID 1926276Notes

Reaction equation

HRID 1926276 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)=[CH:32][CH:31]=[C:30]([O:35]C)[CH:29]=5)[CH:24]=3)[CH:16]=[N:15]2)[CH2:10][CH2:9]1)=O)(C)(C)C.B(Br)(Br)Br.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[NH2:37][C:22]1[C:23]([C:25]2[N:26]=[CH:27][C:28]3[C:33]([CH:34]=2)=[CH:32][CH:31]=[C:30]([OH:35])[CH:29]=3)=[CH:24][C:19]([C:17]2[CH:16]=[N:15][N:14]([CH:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)[CH:18]=2)=[CH:20][N:21]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 25134Boron tribromideHCID 67521135HCID 67521135, compound

Product 1

HCID 67520735HCID 67520735, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Into the DCM (5 ml) solution of 4-{4-[6-amino-5-(7-methoxyisoquinolin-3-yl)-pyridin-3-yl]-pyrazol-1-yl}-piperidine-1-carboxylic acid tert-butyl ester (101 mg, 0.171 mmol), cooled in an ice/water bath, was added 1.00 M of boron tribromide in DCM (2.0 ml) over 5 min. The mixture was stirred at 0° C. and warmed to rt overnight. After that time, the mixture was basified with saturated Na2CO3 until pH 10 and extracted with EtOAc (3×30 ml). The extracts were washed with brine (2×20 ml), dried over MgSO4, filtered and concentrated in vacuo, giving the title compound as a light-yellow solid. 1H NMR (400 MHz, CD3OD): δ=1.90-2.02 (m, 2H), 2.09-2.18 (m, 2H), 2.74-2.82 (m, 2H), 3.18-3.24 (m, 2H), 4.26-4.36 (m, 1H), 7.27 (d, J=2.4 Hz, 1H), 7.36 (dd, J=2.4 & 9.2 Hz, 1H), 7.84-7.87 (m, 2H), 8.06 (d, J=0.8 Hz, 1H), 8.07 (d, J=3.2 Hz, 1H), 8.10 (s, 1H), 8.17 (d, J=2.4 Hz, 1H), 9.08 (s, 1H). MS(ES+): m/z=387.14 (100) [MH+]. HPLC: tR=0.66 & 1.85 min (ZQ3, polar—5 min; peak splitting).

Workup

  1. temperaturewarmed to rt overnight
  2. extractionextracted with EtOAc (3×30 ml)
  3. washThe extracts were washed with brine (2×20 ml)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a76709632acb4054aeef762415933e0b
Source dataset
uspto-grants-2012_05
Patent number
US08178668B2

Reaction notes

Loading…