Trifluoroacetic acid → 1-(5-tert-Butyl-2-p-tolyl-2H-pyrazol-3-yl)-3-[(1S,4R)-4-(3-piperidin-4-ylmethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yloxy)-1,2,3,4-tetrahydro-naphthalen-1-yl]-urea

HRID 1402118Notes

Reaction equation

HRID 1402118 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][C:15]2[N:19]3[CH:20]=[C:21]([O:24][C@H:25]4[C:34]5[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=5)[C@@H:28]([NH:35][C:36]([NH:38][C:39]5[N:40]([C:48]6[CH:53]=[CH:52][C:51]([CH3:54])=[CH:50][CH:49]=6)[N:41]=[C:42]([C:44]([CH3:47])([CH3:46])[CH3:45])[CH:43]=5)=[O:37])[CH2:27][CH2:26]4)[CH:22]=[CH:23][C:18]3=[N:17][N:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:44]([C:42]1[CH:43]=[C:39]([NH:38][C:36]([NH:35][C@@H:28]2[C:29]3[C:34](=[CH:33][CH:32]=[CH:31][CH:30]=3)[C@H:25]([O:24][C:21]3[CH:22]=[CH:23][C:18]4[N:19]([C:15]([CH2:14][CH:11]5[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]5)=[N:16][N:17]=4)[CH:20]=3)[CH2:26][CH2:27]2)=[O:37])[N:40]([C:48]2[CH:49]=[CH:50][C:51]([CH3:54])=[CH:52][CH:53]=2)[N:41]=1)([CH3:47])([CH3:45])[CH3:46]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86686984HCID 86686984, compound

Product 1

HCID 866869851-(5-tert-Butyl-2-p-tolyl-2H-pyrazol-3-yl)-3-[(1S,4R)-4-(3-piperidin-4-ylmethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yloxy)-1,2,3,4-tetrahydro-naphthalen-1-yl]-urea

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

An orange solution of Intermediate 22c (155 mg, 0.211 mmol) and TFA (0.157 mL, 2.11 mmol) in DCM (3 mL) was stirred at RT for 3 h. The solution was concentrated in vacuo, redissolved in MeOH (1 mL), applied to an SCX-2 cartridge (2 g) and washed with MeOH (15 mL). The product was eluted with 2M NH3 in MeOH (15 mL); concentration in vacuo left the title compound as a pale brown solid (116 mg, 87%). LCMS (Method 3): Rt 2.90 min, m/z 633 [MH+].

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. dissolutionredissolved in MeOH (1 mL)
  3. washwashed with MeOH (15 mL)
  4. washThe product was eluted with 2M NH3 in MeOH (15 mL)
  5. concentrationconcentration in vacuo
  6. waitleft the title compound as a pale brown solid (116 mg, 87%)

Sources & evidence

ORD record
ord-b1f063a716724254b19c1da296dd06ff
Source dataset
uspto-grants-2014_12
Patent number
US08907094B2

Reaction notes

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