Hydrochloric Acid → 2-(1-Benzothiophen-7-Yl)-4-[1-(Piperidin-4-Yl)-1h-Pyrazol-4-Yl]furo[2,3-C]pyridin-7-Amine

HRID 389493Notes

Reaction equation

HRID 389493 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:20]2[CH:21]=[N:22][N:23]([CH:25]3[CH2:30][CH2:29][N:28](C(OC(C)(C)C)=O)[CH2:27][CH2:26]3)[CH:24]=2)=[C:6]2[CH:10]=[C:9]([C:11]3[C:19]4[S:18][CH:17]=[CH:16][C:15]=4[CH:14]=[CH:13][CH:12]=3)[O:8][C:7]=12.Cl>C(Cl)Cl>[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:20]2[CH:21]=[N:22][N:23]([CH:25]3[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]3)[CH:24]=2)=[C:6]2[CH:10]=[C:9]([C:11]3[C:19]4[S:18][CH:17]=[CH:16][C:15]=4[CH:14]=[CH:13][CH:12]=3)[O:8][C:7]=12

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66760630tert-butyl 4-{4-[7-amino-2-(1-benzothiophen-7-yl)furo[2,3-c]pyridine-4-yl]-1H-pyrazol-1-yl}piperidine-1-carboxylate

Product 1

HCID 533792532-(1-Benzothiophen-7-Yl)-4-[1-(Piperidin-4-Yl)-1h-Pyrazol-4-Yl]furo[2,3-C]pyridin-7-AmineYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl 4-{4-[7-amino-2-(1-benzothiophen-7-yl)furo[2,3-c]pyridine-4-yl]-1H-pyrazol-1-yl}piperidine-1-carboxylate in DCM (1.50 mL) was treated with HCl (1 M in Et2O, 5.00 mL, 5.00 mmol) and stirred for 30 min. The reaction was concentrated in vacuo to afford 86 mg (71%) of the title compound. 1H NMR (400 MHz, CD3OD) δ 7.08 (s, 1 H), 7.00 (d, J=7.58 Hz, 1 H), 6.82 (d, J=7.83 Hz, 1 H), 6.79 (s, 1 H), 6.59 (s, 1 H), 6.50-6.54 (m, 2 H), 6.36 (t, J=7.71 Hz, 1 H), 6.32 (d, J=5.56 Hz, 1 H), 3.39-3.52 (m, 1 H), 2.36 (d, J=13.14 Hz, 2 H), 1.96-2.02 (m, 2 H), 1.09-1.19 (m, 4 H); MS (ESI): 416.12 [M+H]+; HPLC tR=2.19 min.

Workup

  1. concentrationThe reaction was concentrated in vacuo

Sources & evidence

ORD record
ord-2c3e714e44fc4fb797ed69d5ca8f08f6
Source dataset
uspto-grants-2013_02
Patent number
US08378104B2

Reaction notes

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