Trifluoroacetic acid → HCID 16116992, compound

HRID 1712989Notes

Reaction equation

HRID 1712989 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([S:14]([C:17]2[CH:22]=[CH:21][C:20]([CH:23]([C:30](=[O:47])[NH:31][C:32]3[S:33][C:34]4[C:39]([N:40]=3)=[CH:38][CH:37]=[C:36]([N:41]3[CH2:46][CH2:45][O:44][CH2:43][CH2:42]3)[N:35]=4)[CH2:24][CH:25]3[CH2:29][CH2:28][CH2:27][CH2:26]3)=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH:25]1([CH2:24][CH:23]([C:20]2[CH:19]=[CH:18][C:17]([S:14]([N:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)(=[O:16])=[O:15])=[CH:22][CH:21]=2)[C:30]([NH:31][C:32]2[S:33][C:34]3[C:39]([N:40]=2)=[CH:38][CH:37]=[C:36]([N:41]2[CH2:42][CH2:43][O:44][CH2:45][CH2:46]2)[N:35]=3)=[O:47])[CH2:29][CH2:28][CH2:27][CH2:26]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59463481HCID 59463481, compound

Product 1

HCID 16116992HCID 16116992, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Title compound G, 4-{4-[2-Cyclopentyl-1-(5-morpholin-4-yl-thiazolo[5,4-b]pyridin-2-ylcarbamoyl)-ethyl]-benzenesulfonyl}-piperazine-1-carboxylic acid tert-butyl ester (0.26 g, 0.378 mmol) was dissolved in 5 mL DCM and 2 mL of TFA was added. The solution was stirred for 1 h and then evaporated to afford a crude oil. The residue was partitioned between 2N NaOH and ethyl acetate and extracted numerous times with ethyl acetate, dried over MgSO4, filtered and concentrated to afford a green solid. This material was taken on crude to the next reaction. 1H NMR (400 MHz, DMSO) δ 1.07-1.16 (M, 2H) 1.39-1.50 (m, 2H) 1.52-1.63 (m, 3H) 1.68-1.79 (m, 3H) 2.16 (m, 1H) 2.71 (d, J=4.80 Hz, 4H) 2.76 (d, J=5.05 Hz, 4H) 3.43-3.51 (m, 4H) 3.67-3.74 (m, 4H) 4.07 (d, J=8.84 Hz, 1H) 6.97 (d, J=9.09 Hz, 1H) 7.64-7.69 (m, 2H) 7.69-7.73 (m, 2H) 7.88 (d, J=9.09 Hz, 1H) MS 585.31 [M+1]+.

Workup

  1. customevaporated
  2. customto afford a crude oil
  3. customThe residue was partitioned between 2N NaOH and ethyl acetate
  4. extractionextracted numerous times with ethyl acetate
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto afford a green solid
  9. customThis material was taken on crude to the next reaction

Sources & evidence

ORD record
ord-ad4125ffa08c459dac84b0c61207415b
Source dataset
uspto-grants-2010_09
Patent number
US07795257B2

Reaction notes

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