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 2282393Notes

Reaction equation

HRID 2282393 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-3b0abd9808134bf2a1e1076dae7ef68f
Source dataset
uspto-grants-2015_09
Patent number
US09139584B2

Reaction notes

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