Trifluoroacetic acid → HCID 18382874, compound

HRID 2297846Notes

Reaction equation

HRID 2297846 reaction equation
C(OC([N:8]1[CH:12]=[CH:11][CH:10]=[C:9]1[C:13]1[S:21][C:20]2[C:15](=[N:16][CH:17]=[CH:18][C:19]=2[NH:22][C:23]2[CH:24]=[C:25]3[C:29](=[CH:30][CH:31]=2)[NH:28][C:27]([CH3:32])=[CH:26]3)[CH:14]=1)=O)(C)(C)C.FC(F)(F)C(O)=O.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl.O>[CH3:32][C:27]1[NH:28][C:29]2[C:25]([CH:26]=1)=[CH:24][C:23]([NH:22][C:19]1[CH:18]=[CH:17][N:16]=[C:15]3[CH:14]=[C:13]([C:9]4[NH:8][CH:12]=[CH:11][CH:10]=4)[S:21][C:20]=13)=[CH:31][CH:30]=2

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 69993817HCID 69993817, compound

Product 1

HCID 18382874HCID 18382874, compoundYield 62.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 2-[7-(2-methyl-1H-indol-5-ylamino)-thieno[3,2-b]pyridin-2-yl]-pyrrole-1-carboxylic acid tert-butyl ester (131 mg, 0.29 mmol) and trifluoroacetic acid (0.1 mL) in dichloromethane (1 mL) was stirred overnight. The solution was diluted with dichloromethane and water, and the pH was adjusted to 8.0 with a saturated aqueous sodium carbonate solution. The organic layer was dried over Na2SO4 and concentrated to afford (2-methyl-1H-indol-5-yl)-[2-(1H-pyrrol-2-yl)-thieno[3,2-b]pyridin-7-yl]-amine (62 mg, 56%). 1H NMR (400 MHz, CD3OD) δ7.93 (d, 1H), 7.25 (m, 3H), 6.93 (dd, 1H), 6.83 (s, 1H, 6.44 (dd, 1H), 6.13 (dd, 1H), 6.07 (s, 1H), 2.37 (s, 3H); RP18-HPLC RT: 5.45 minutes; API MS: 345 (M+1).

Workup

  1. dry with materialThe organic layer was dried over Na2SO4
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-a5949c17956e4b41b8b5f6a8e068460a
Source dataset
uspto-grants-2002_12
Patent number
US06492383B1

Reaction notes

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