Trifluoroacetic acid → Trifluoroacetic acid

HRID 1484888Notes

Reaction equation

HRID 1484888 reaction equation
[NH2:1]/[C:2](=[N:24]\C(=O)OC(C)(C)C)/[C:3]1[S:4][C:5]([C:8]2[N:13]=[C:12]([NH:14][C:15]3[CH:19]=[C:18]([CH:20]4[CH2:22][CH2:21]4)[NH:17][N:16]=3)[C:11]([Cl:23])=[CH:10][N:9]=2)=[CH:6][CH:7]=1.[C:32]([OH:38])([C:34]([F:37])([F:36])[F:35])=[O:33]>C(Cl)Cl>[Cl:23][C:11]1[C:12]([NH:14][C:15]2[CH:19]=[C:18]([CH:20]3[CH2:21][CH2:22]3)[NH:17][N:16]=2)=[N:13][C:8]([C:5]2[S:4][C:3]([C:2](=[NH:1])[NH2:24])=[CH:7][CH:6]=2)=[N:9][CH:10]=1.[C:32]([OH:38])([C:34]([F:37])([F:36])[F:35])=[O:33]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58169186HCID 58169186, compound2×

Product 2

HCID 6422Trifluoroacetic acidYield 72%HCID 50942857HCID 50942857, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of (Z)-tert-butyl amino(5-(5-chloro-4-(5-cyclopropyl-1H-pyrazol-3-ylamino)pyrimidin-2-yl)thiophen-2-yl)methylenecarbamate (Compound 328) (60 mg, 0.13 mmol) and TFA (2 mL) in DCM (2 mL) was stirred at room temperature for 1 h. The solvent was distilled and recrystallized with ether (2 mL) to afford get 5-(5-chloro-4-(5-cyclopropyl-1H-pyrazol-3-ylamino)pyrimidin-2-yl)thiophene-2-carboximidamide (Compound 205) as TFA salt (55 mg, 72%). LC-MS (m/z)=360 [M+H]+; 1H NMR (400 MHz, DMSO-d6): δ 0.77-0.81 (m, 2H), 0.97-1.01 (m, 2H), 1.97-2.01 (m, 1H), 6.43 (s, 1H), 7.90 (d, J=4.0 Hz, 1H), 8.01 (d, J=4.0 Hz, 1H), 8.50 (s, 1H), 9.34 (s, 2H), 9.44 (s, 2H), 9.56 (s, 1H).

Workup

  1. distillationThe solvent was distilled
  2. customrecrystallized with ether (2 mL)
  3. customto afford

Sources & evidence

ORD record
ord-bc47cf4c5577406ebb78e8914ca79f28
Source dataset
uspto-grants-2016_08
Patent number
US09422271B2

Reaction notes

Loading…