Trifluoroacetic acid → HCID 136338259, compound

HRID 1529454Notes

Reaction equation

HRID 1529454 reaction equation
[CH:1]1([C:4]2[N:9]=[C:8]([C:10]3[CH:11]=[C:12]4[C:16](=[CH:17][CH:18]=3)[NH:15][CH:14]=[C:13]4[C:19]3[CH:24]=[C:23]([O:25]CC4C=CC(OC)=CC=4)[N:22]=[C:21]([NH:35][CH:36]([CH3:38])[CH3:37])[N:20]=3)[CH:7]=[N:6][CH:5]=2)[CH2:3][CH2:2]1.C(O)(C(F)(F)F)=O>>[CH:1]1([C:4]2[N:9]=[C:8]([C:10]3[CH:11]=[C:12]4[C:16](=[CH:17][CH:18]=3)[NH:15][CH:14]=[C:13]4[C:19]3[N:20]=[C:21]([NH:35][CH:36]([CH3:37])[CH3:38])[NH:22][C:23](=[O:25])[CH:24]=3)[CH:7]=[N:6][CH:5]=2)[CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 67959746HCID 67959746, compound

Product 1

HCID 136338259HCID 136338259, compoundYield 15.8%

Conditions

Temperature
120 °C

Procedure

A glass microwave reaction vessel was charged with 4-(5-(6-cyclopropylpyrazin-2-yl)-1H-indol-3-yl)-N-isopropyl-6-(4-methoxybenzyloxy)pyrimidin-2-amine (25 mg, 0.049 mmol) and TFA (1 mL, 12.98 mmol). The reaction was stirred and heated in a Initiator microwave reactor (Personal Chemistry, Biotage AB, Inc., Upssala, Sweden) at 120° C. for 20 min, then the solvent was removed and the residue was purified with RP-HPLC (10-50% ACN in water with 0.1% TFA) to give 6-(5-(6-cyclopropylpyrazin-2-yl)-1H-indol-3-yl)-2-(isopropylamino)pyrimidin-4(3H)-one (3.0 mg, 7.76 μmol, 15.73% yield) as a TFA salt. MS (ESI, pos. ion) m/z: 387.0 (M+1); 1H NMR (400 MHz, DMSO-d6) δ ppm 11.82 (1 H, br. s.), 8.82-9.07 (2 H, m), 8.48 (1 H, s), 8.14 (1 H, d, J=2.3 Hz), 7.88 (1 H, d, J=8.2 Hz), 7.56 (1 H, d, J=8.8 Hz), 6.10 (1 H, br. s.), 4.20-4.36 (1 H, m), 2.19-2.31 (1 H, m), 1.27 (6 H, d, J=6.5 Hz), 1.04-1.14 (4 H, m)

Workup

  1. customA glass microwave reaction vessel
  2. customthe solvent was removed
  3. customthe residue was purified with RP-HPLC (10-50% ACN in water with 0.1% TFA)

Sources & evidence

ORD record
ord-4ac944d8e7ff41c49c972dc5fdea5c4a
Source dataset
uspto-grants-2015_07
Patent number
US09090593B2

Reaction notes

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