Trifluoroacetic acid → HCID 86296948, compound

HRID 930829Notes

Reaction equation

HRID 930829 reaction equation
C(O[C:6](=O)[N:7]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[N:17][C:18]3[N:19]([CH:21]=[C:22]([C:24]4[CH:29]=[C:28]([NH:30][C:31]([N:33]5[CH2:37][CH2:36][CH2:35][CH2:34]5)=[O:32])[CH:27]=[CH:26][C:25]=4[Cl:38])[N:23]=3)[CH:20]=2)=[CH:11][CH:10]=1)C)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:38][C:25]1[CH:26]=[CH:27][C:28]([NH:30][C:31]([N:33]2[CH2:34][CH2:35][CH2:36][CH2:37]2)=[O:32])=[CH:29][C:24]=1[C:22]1[N:23]=[C:18]2[N:17]=[CH:16][C:15]([C:12]3[CH:11]=[CH:10][C:9]([NH:7][CH3:6])=[CH:14][CH:13]=3)=[CH:20][N:19]2[CH:21]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 90410825HCID 90410825, compound

Product 1

HCID 86296948HCID 86296948, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-butyl(4-(2-(2-chloro-5-(pyrrolidine-1-carboxamido)phenyl)imidazo[1,2-a]pyrimidin-6-yl)phenyl)(methyl)carbamate was treated with 5% TFA in DCM and was stirred overnight at room temperature. At completion, the reaction mixture was concentrated in vacuo and the residue was redissolved in methanol. Purification of the compound was done via mass-triggered reverse phase column chromatography preparative system (15% to 65% (B)). m/z (ESI) for 26: 447.2 (M+H+), 1H NMR (600 MHz, DMSO-D6) δ 9.17 (d, J=2.6, 1H), 8.88 (d, J=2.6, 1H), 8.5, 362 (s, 1H), 8.46 (m, 2H), 7.73 (m, 1H), 7.52 (d, J=8.6, 2H), 7.40 (d, J=8.8, 1H), 6.68 (d, J=8.7, 2H), 5.97 (s, 1H), 3.40 (s, 4H), 2.73 (d, J=5.0, 3H), 1.86 (s, 4H).

Workup

  1. concentrationAt completion, the reaction mixture was concentrated in vacuo
  2. dissolutionthe residue was redissolved in methanol
  3. customPurification of the compound

Sources & evidence

ORD record
ord-002f343c1fb74172afa2fa4a52178cef
Source dataset
uspto-grants-2016_03
Patent number
US09296754B2

Reaction notes

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