Trifluoroacetic acid → HCID 131730619, compound

HRID 1256361Notes

Reaction equation

HRID 1256361 reaction equation
[OH:1][C:2]([C:5]1[CH:39]=[CH:38][C:8]([C:9]([NH:11][C:12]2[CH:17]=[C:16]([C:18]3[CH:27]=[C:26]4[C:21]([CH2:22][CH2:23][N:24](C(OC(C)(C)C)=O)[CH2:25]4)=[CH:20][CH:19]=3)[N:15]3[N:35]=[CH:36][CH:37]=[C:14]3[N:13]=2)=[O:10])=[CH:7][CH:6]=1)([CH3:4])[CH3:3].[F:40][C:41]([F:46])([F:45])[C:42]([OH:44])=[O:43]>C(Cl)Cl>[F:40][C:41]([F:46])([F:45])[C:42]([OH:44])=[O:43].[OH:1][C:2]([C:5]1[CH:6]=[CH:7][C:8]([C:9]([NH:11][C:12]2[CH:17]=[C:16]([C:18]3[CH:27]=[C:26]4[C:21]([CH2:22][CH2:23][NH:24][CH2:25]4)=[CH:20][CH:19]=3)[N:15]3[N:35]=[CH:36][CH:37]=[C:14]3[N:13]=2)=[O:10])=[CH:38][CH:39]=1)([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67064824HCID 67064824, compound

Product 1

HCID 131730619HCID 131730619, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 7-(5-(4-(2-hydroxypropan-2-yl)benzamido)pyrazolo[1,5-a]pyrimidin-7-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate from Step A was dissolved in CH2Cl2 (2 ml). Trifluoroacetic acid (2 ml) was then added at 0° C. The mixture was stirred for 30 minutes at that temperature before being concentrated in vacuo. Residual trifluoroacetic acid was removed azeotropically with toluene twice. The residue was then dissolved in acetonitrile before being purified by preparatory HPLC (20-30% MeCN/H2O gradient+0.01% TFA) to give the titled compound as a white powder (50 mg, 41% yield). 1H NMR (400 MHz, DMSO-d6) δ=11.30 (s, 1 H), 9.14 (br. s., 2 H), 8.21 (d, J=2.5 Hz, 1 H), 8.07 (s, 1 H), 8.05-8.01 (m, 2 H), 8.00-7.95 (m, 1 H), 7.65-7.60 (m, 2 H), 7.50 (d, J=8.1 Hz, 1 H), 6.60 (d, J=2.3 Hz, 1 H), 4.47-4.40 (m, 2 H), 3.47 (br. s., 2 H), 3.13 (t, J=6.2 Hz, 2 H), 1.46 (s, 6 H).

Workup

  1. concentrationbefore being concentrated in vacuo
  2. customResidual trifluoroacetic acid was removed azeotropically with toluene twice
  3. dissolutionThe residue was then dissolved in acetonitrile
  4. custombefore being purified by preparatory HPLC (20-30% MeCN/H2O gradient+0.01% TFA)

Sources & evidence

ORD record
ord-554bddc898ab4f8582504217c23d66c3
Source dataset
uspto-grants-2013_06
Patent number
US08461163B2

Reaction notes

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