Trifluoroacetic acid → HCID 86614646, compound

HRID 1676279Notes

Reaction equation

HRID 1676279 reaction equation
[CH2:1]([N:3]([CH2:41][CH3:42])[CH2:4][C:5]#[C:6][C:7]1[S:15][C:14]2[C:9](=[N:10][CH:11]=[CH:12][C:13]=2[O:16][C:17]2[CH:22]=[CH:21][C:20]([NH:23][C:24](=[O:39])[CH2:25][CH:26]3[CH2:31][CH2:30][N:29](C(OC(C)(C)C)=O)[CH2:28][CH2:27]3)=[CH:19][C:18]=2[F:40])[CH:8]=1)[CH3:2].[F:43][C:44]([F:49])([F:48])[C:45]([OH:47])=[O:46]>C(Cl)Cl>[F:43][C:44]([F:49])([F:48])[C:45]([OH:47])=[O:46].[F:43][C:44]([F:49])([F:48])[C:45]([OH:47])=[O:46].[CH2:41]([N:3]([CH2:1][CH3:2])[CH2:4][C:5]#[C:6][C:7]1[S:15][C:14]2[C:9](=[N:10][CH:11]=[CH:12][C:13]=2[O:16][C:17]2[CH:22]=[CH:21][C:20]([NH:23][C:24](=[O:39])[CH2:25][CH:26]3[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]3)=[CH:19][C:18]=2[F:40])[CH:8]=1)[CH3:42]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 24983364HCID 24983364, compound

Product 1

HCID 86614646HCID 86614646, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of tert-butyl 4-(2-(4-(2-(3-(diethylamino)prop-1-ynyl)thieno[3,2-b]pyridin-7-yloxy)-3-fluorophenylamino)-2-oxoethyl)piperidine-1-carboxylate (Example 35; 2 mg, 0.00336 mmol) in methylene chloride (3 mL) was added 2,2,2-trifluoroacetic acid (3.83 mg, 0.0336 mmol). The reaction was stirred for 4 hours at room temperature. The reaction mixture was concentrated to dryness to give the product as a clear oil. Yield: 1.2 mg (47%). LRMS (esi pos) m/e 495 (M+1).

Workup

  1. concentrationThe reaction mixture was concentrated to dryness

Sources & evidence

ORD record
ord-cdf8ef9a6b8a4adaa68997fb2d24dee3
Source dataset
uspto-grants-2011_08
Patent number
US08003662B2

Reaction notes

Loading…