Trifluoroacetic acid → HCID 89735655, compound

HRID 1842601Notes

Reaction equation

HRID 1842601 reaction equation
C(OC(=O)[NH:7][C@@H:8]1[CH2:13][CH2:12][CH2:11][C:10]([F:15])([F:14])[C@@H:9]1[NH:16][C:17]([C:19]1[S:20][C:21]([CH3:34])=[C:22]([C:24]2[CH:25]=[N:26][N:27]3[CH:32]=[C:31]([Cl:33])[CH:30]=[N:29][C:28]=23)[CH:23]=1)=[O:18])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH2:7][C@H:8]1[C@@H:9]([NH:16][C:17]([C:19]2[S:20][C:21]([CH3:34])=[C:22]([C:24]3[CH:25]=[N:26][N:27]4[CH:32]=[C:31]([Cl:33])[CH:30]=[N:29][C:28]=34)[CH:23]=2)=[O:18])[C:10]([F:15])([F:14])[CH2:11][CH2:12][CH2:13]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68304938HCID 68304938, compound

Product 1

HCID 89735655HCID 89735655, compoundYield 90.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To tert-butyl-[(1R,2R)-2-({[4-(6-chloropyrazolo[1,5-a]pyrimidin-3-yl)-5-methylthiophen-2-yl]carbonyl}amino)-3,3-difluorocyclohexyl]carbamate (3.36 g, 6.39 mmol) in dichloromethane (10 mL) was added trifluoroacetic acid (10 mL, 130 mmol) and stirred for 16 h at ambient temperature. The reaction was evaporated to dryness, partitioned dichloromethane and saturated sodium bicarbonate. The aqueous layer was extracted with dichloromethane 3×. The organic layers were combined, dried with sodium sulfate, filtered, and concentrated under reduced pressure to afford the title compound (2.46 g, 5.77 mmol). LRMS (APCI) calc'd for (C18H18ClF2N5OS) [M+H]+, 426.1; found 426.0. 1H NMR (CDCl3, 500 MHz) δ 8.74 (s, 1H), 8.48 (s, 1H), 8.25 (s, 1H), 7.91 (s, 1H), 6.98 (d, J=9.3, 1H), 4.46 (d, J=25.3, 1H), 3.34 (m, 1H), 2.57 (s, 3H), 2.18 (m, 1H), 1.67-1.90 (m, 5H).

Workup

  1. customThe reaction was evaporated to dryness
  2. custompartitioned dichloromethane and saturated sodium bicarbonate
  3. extractionThe aqueous layer was extracted with dichloromethane 3×
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-58e804e6d6bf407ebd46814768fd79aa
Source dataset
uspto-grants-2015_02
Patent number
US08946237B2

Reaction notes

Loading…