Trifluoroacetic acid → (+/-)-3-Amino-5,7-dihydrospiro[cyclopenta[c]pyridine-6,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one trifluoroacetate

HRID 1615807Notes

Reaction equation

HRID 1615807 reaction equation
[O:1]=[C:2]1[NH:10][C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]21[CH2:26][C:13]1[CH:14]=[N:15][C:16]([NH:18]C(=O)OC(C)(C)C)=[CH:17][C:12]=1[CH2:11]2.[C:27]([OH:33])([C:29]([F:32])([F:31])[F:30])=[O:28]>C(Cl)Cl>[F:30][C:29]([F:32])([F:31])[C:27]([OH:33])=[O:28].[NH2:18][C:16]1[N:15]=[CH:14][C:13]2[CH2:26][C:3]3([CH2:11][C:12]=2[CH:17]=1)[C:4]1[C:5](=[N:6][CH:7]=[CH:8][CH:9]=1)[NH:10][C:2]3=[O:1]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86616403(+/-)-Tert-butyl(2'-oxo-1',2',5,7-tetrahydrospiro[cyclopenta[c]pyridine-6,3'-pyrrolo[2,3-b]pyridin]-3-yl)carbamate

Product 1

HCID 66812778(+/-)-3-Amino-5,7-dihydrospiro[cyclopenta[c]pyridine-6,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one trifluoroacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (±)-tert-butyl (2′-oxo-1′,2′,5,7-tetrahydrospiro[cyclopenta[c]pyridine-6,3′-pyrrolo[2,3-b]pyridin]-3-yl)carbamate from Step A (131 mg, 0.372 mmol) was stirred in CH2Cl2 (10 mL) and TFA (3 mL) for 18 h and then concentrated in vacuo to provide the title compound. MS: m/z=253 (M+1).

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4a02a392816b406ebd0d10a251497bbc
Source dataset
uspto-grants-2014_07
Patent number
US08765759B2

Reaction notes

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