Trifluoroacetic acid → 9-cyclopentyl-N-(4-(1-piperazinylcarbonyl)-1,3-thiazol-2-yl)-9H-pyrido[4',3':4,5]pyrrolo-[2,3-d]pyrimidin-2-amine

HRID 875949Notes

Reaction equation

HRID 875949 reaction equation
[CH:1]1([N:6]2[C:10]3[N:11]=[C:12]([NH:15][C:16]4[S:17][CH:18]=[C:19]([C:21]([N:23]5[CH2:28][CH2:27][N:26](C(OC(C)(C)C)=O)[CH2:25][CH2:24]5)=[O:22])[N:20]=4)[N:13]=[CH:14][C:9]=3[C:8]3[CH:36]=[CH:37][N:38]=[CH:39][C:7]2=3)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH:1]1([N:6]2[C:10]3[N:11]=[C:12]([NH:15][C:16]4[S:17][CH:18]=[C:19]([C:21]([N:23]5[CH2:24][CH2:25][NH:26][CH2:27][CH2:28]5)=[O:22])[N:20]=4)[N:13]=[CH:14][C:9]=3[C:8]3[CH:36]=[CH:37][N:38]=[CH:39][C:7]2=3)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 582999641,1-dimethylethyl 4-((2-((9-cyclopentyl-9H-pyrido[4',3':4,5]pyrrolo[2,3-d]pyrimidin-2-yl)amino)-1,3-thiazol-4-yl)carbonyl)-1-piperazinecarboxylate

Product 1

HCID 582999949-cyclopentyl-N-(4-(1-piperazinylcarbonyl)-1,3-thiazol-2-yl)-9H-pyrido[4',3':4,5]pyrrolo-[2,3-d]pyrimidin-2-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound 74 was dissolved in DCM (5 mL) and TFA (1.5 mL) and stirred at 20° C. for 2.5 hrs. The reaction was concentrated in vacuum and purified by preparative HPLC eluting with a gradient 10% MeCN/water/0.1% TFA-50% MeCN/water/0.1% TFA to provide compound 71 (23 mg) as a yellow solid. 1H NMR (500 MHz, CD3OD) δ 9.63 (1H, s), 9.32 (1H, s), 8.68 (1H, d, J=6.1 Hz), 8.63 (1H, d, J=6.4 Hz), 7.84 (1H, s), 5.56 (1H, p, J=8.1), 4.00-4.29 (4H, br s), 3.39 (4H, t, J=5.3 Hz), 2.63 (2H, m), 2.25 (4H, m), 1.98 (2H, m) ppm; LCMS-ESI (POS), M/Z, M+1: Found 449.2.

Workup

  1. concentrationThe reaction was concentrated in vacuum
  2. custompurified by preparative HPLC
  3. washeluting with a gradient 10% MeCN/water/0.1% TFA-50% MeCN/water/0.1% TFA

Sources & evidence

ORD record
ord-e63569ae97d6428ea308766f83173de1
Source dataset
uspto-grants-2015_03
Patent number
US08980903B2

Reaction notes

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