Hydrochloric Acid → HCID 66759801, compound

HRID 389494Notes

Reaction equation

HRID 389494 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[CH:12]=[C:13]4[C:17](=[CH:18][CH:19]=3)[NH:16][N:15]=[CH:14]4)[O:8][C:7]=12.[ClH:38]>CCOC(C)=O>[ClH:38].[NH:16]1[C:17]2[C:13](=[CH:12][C:11]([C:9]3[O:8][C:7]4=[C:2]([NH2:1])[N:3]=[CH:4][C:5]([C:20]5[CH:21]=[N:22][N:23]([CH:25]6[CH2:26][CH2:27][NH:28][CH2:29][CH2:30]6)[CH:24]=5)=[C:6]4[CH:10]=3)=[CH:19][CH:18]=2)[CH:14]=[N:15]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66759857HCID 66759857, compound

Product 1

HCID 66759801HCID 66759801, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of crude tert-butyl 4-{4-[7-amino-2-(1H-indazol-5-yl)furo[2,3-c]pyridine-4-yl]-1H-pyrazol-1-yl}piperidine-1-carboxylate (from Step A) in EtOAc was treated with HCl (4 M in EtOAc, 5 mL, 5 mmol) for 60 min. The reaction was filtered to afford 24 mg (60%) of the title compound. 1H NMR (400 MHz, CD3OD): δ 8.89 (s, 1 H), 8.41 (s, 1 H), 8.08 (s, 1 H), 8.04 (d, J=7.07 Hz, 1 H), 7.89 (s, 1 H), 7.86 (s, 1 H), 7.78 (d, J=8.59 Hz, 1 H), 7.57-7.63 (m, 1 H), 4.67-4.77 (m, 1 H), 3.57-3.65 (m, 2 H), 3.22-3.29 (m, 2 H), 2.37-2.46 (m, 4 H); MS (ESI): 400.09 [M+H]+; HPLC tR=1.81 min.

Workup

  1. filtrationThe reaction was filtered

Sources & evidence

ORD record
ord-088390a3ddc248beaedec6430602daaf
Source dataset
uspto-grants-2013_02
Patent number
US08378104B2

Reaction notes

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