Trifluoroacetic acid → HCID 68709997, compound

HRID 2239374Notes

Reaction equation

HRID 2239374 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:16][C:15]3[C:14](=[O:17])[N:13]([CH2:18][C:19]4[N:24]=[C:23]([O:25][CH:26]5[CH2:31][CH2:30][N:29](C(OC(C)(C)C)=O)[CH2:28][CH2:27]5)[CH:22]=[CH:21][CH:20]=4)[CH:12]=[N:11][C:10]=3[CH:9]=2)=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:16][C:15]3[C:14](=[O:17])[N:13]([CH2:18][C:19]4[CH:20]=[CH:21][CH:22]=[C:23]([O:25][CH:26]5[CH2:27][CH2:28][NH:29][CH2:30][CH2:31]5)[N:24]=4)[CH:12]=[N:11][C:10]=3[CH:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 86618696HCID 86618696, compound

Product 1

HCID 68709997HCID 68709997, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

tert-Butyl 4-[(6-{[6-(4-chlorophenyl)-4-oxothieno[3,2-d]pyrimidin-3(4H)-yl]methyl}pyridin-2-yl)oxy]piperidine-1-carboxylate (679 mg, 1.23 mmol) was dissolved in DCM (5 ml) and TFA (1 ml) added. The reaction was stirred at rt. for 40 minutes. DCM (150 ml) and sat. Na2CO3 (aq) (150 ml) were added, the phases separated and the aqueous phase extracted with DCM (150 ml). The combined organics were dried through a phase separator and evaporated in vacuo to yield the title compound as a colorless oil. Yield: 550 mg (99%). 1H NMR (400 MHz, CDCl3) δ 8.29 (s, 1H), 7.63 (m, 2H), 7.55 (dd, 1H, J=8.0 Hz, J=7.4 Hz), 7.48 (s, 1H), 7.42 (m, 2H), 6.95 (d, 1H, J=7.2 Hz), 6.61 (d, 1H, J=8.2 Hz), 5.20 (s, 2H), 4.90 (m, 1H), 3.01 (m, 2H), 2.61 (m, 2H), 1.87 (m, 2H), 1.60-1.46 (m, 3H). 13C NMR (400 MHz, CDCl3) δ 163.2, 157.9, 157.1, 151.6, 151.4, 149.3, 139.8, 135.8, 131.8, 129.6, 127.8, 123.1, 121.0, 115.0, 111.3, 71.9, 50.2, 44.4, 32.6. MS (ESI+) 453.00 (M+1H+)

Workup

  1. customthe phases separated
  2. extractionthe aqueous phase extracted with DCM (150 ml)
  3. customThe combined organics were dried through a phase separator
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-a8f4c859caff42cd9ae60a9a61121064
Source dataset
uspto-grants-2010_05
Patent number
US07723331B2

Reaction notes

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