Trifluoroacetic acid → HCID 131732204, compound

HRID 1409241Notes

Reaction equation

HRID 1409241 reaction equation
[OH:1][C:2]([C:5]1[CH:36]=[CH:35][C:8]([C:9]([NH:11][C:12]2[CH:17]=[C:16]([N:18]3[CH2:23][CH2:22][CH2:21][C@@H:20]([NH:24]C(=O)OC(C)(C)C)[CH2:19]3)[N:15]3[N:32]=[CH:33][CH:34]=[C:14]3[N:13]=2)=[O:10])=[CH:7][CH:6]=1)([CH3:4])[CH3:3].[F:37][C:38]([F:43])([F:42])[C:39]([OH:41])=[O:40]>C(Cl)Cl>[F:37][C:38]([F:43])([F:42])[C:39]([OH:41])=[O:40].[NH2:24][C@@H:20]1[CH2:21][CH2:22][CH2:23][N:18]([C:16]2[N:15]3[N:32]=[CH:33][CH:34]=[C:14]3[N:13]=[C:12]([NH:11][C:9](=[O:10])[C:8]3[CH:35]=[CH:36][C:5]([C:2]([OH:1])([CH3:3])[CH3:4])=[CH:6][CH:7]=3)[CH:17]=2)[CH2:19]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89724340HCID 89724340, compound

Product 1

HCID 131732204HCID 131732204, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(R)-tert-butyl 1-(5-(4-(2-hydroxypropan-2-yl)benzamido)pyrazolo[1,5-a]pyrimidin-7-yl)piperidin-3-ylcarbamate was dissolved in CH2Cl2. Trifluoroacetic acid was added and the mixture was let stirred for 6 hours. The reaction mixture was concentrated to dryness in vacuo, and part of the residue was purified by preparatory HPLC (20-50% MeCN/H2O gradient+0.01% TFA). Lyophilization of the combined fractions gave the titled compound as a white powder. 1H NMR (400 MHz, DMSO-d6) δ=10.97 (s, 1H), 8.13 (d, J=2.3 Hz, 1H), 8.11-8.03 (m, 2H), 8.03-7.97 (m, 2H), 7.64-7.57 (m, 2H), 7.48 (s, 1H), 6.40 (d, J=2.3 Hz, 1H), 4.23 (br. s., 1H), 3.97 (br. s., 2H), 3.47 (d, J=7.1 Hz, 2H), 3.28 (br. s., 1H), 2.08 (br. s., 1H), 1.96 (br. s., 1H), 1.85-1.64 (m, 2H), 1.46 (s, 6H); ESI-MS: m/z 377.4 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated to dryness in vacuo, and part of the residue
  2. customwas purified by preparatory HPLC (20-50% MeCN/H2O gradient+0.01% TFA)

Sources & evidence

ORD record
ord-fb7fd4dfd3834f11b57fe84f9b0b0645
Source dataset
uspto-grants-2014_12
Patent number
US08921358B2

Reaction notes

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