Trifluoroacetic acid methylene chloride → 5-(3-Fluoro-2'-{[(2R)-2-methylpiperazin-1-yl]sulfonyl}biphenyl-4-yl)pyrimidin-2-amine

HRID 1523865Notes

Reaction equation

HRID 1523865 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[S:20]([N:23]3[CH2:28][CH2:27][N:26](C(OC(C)(C)C)=O)[CH2:25][C@H:24]3[CH3:36])(=[O:22])=[O:21])=[CH:10][C:9]=2[F:37])=[CH:4][N:3]=1.C(Cl)Cl.C(O)(C(F)(F)F)=O>>[F:37][C:9]1[CH:10]=[C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[S:20]([N:23]2[CH2:28][CH2:27][NH:26][CH2:25][C@H:24]2[CH3:36])(=[O:22])=[O:21])[CH:12]=[CH:13][C:8]=1[C:5]1[CH:6]=[N:7][C:2]([NH2:1])=[N:3][CH:4]=1

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 90313269(R)-tert-Butyl 4-((4'-(2-aminopyrimidin-5-yl)-3'-fluoro-[1,1'-biphenyl]-2-yl)sulfonyl)-3-methylpiperazine-1-carboxylate

Product 1

HCID 903133885-(3-Fluoro-2'-{[(2R)-2-methylpiperazin-1-yl]sulfonyl}biphenyl-4-yl)pyrimidin-2-amineYield 85%

Procedure

The title compound was prepared by dissolving (R)-tert-butyl 4-((4′-(2-aminopyrimidin-5-yl)-3′-fluoro-[1,1′-biphenyl]-2-yl)sulfonyl)-3-methylpiperazine-1-carboxylate (42 mg, 0.08 mmol) in a 50/50 mixture of DCM/TFA (1 mL) and allowing it to stir at rt for 2 h. The reaction mixture was concentrated to dryness and the residue subjected to HPLC purification to give the title compound (29 mg, 85%). MS (ESI): mass calcd. for C21H22FN5O2S, 427.15; m/z found, 428.1 [M+H]+. 1H NMR (400 MHz, CDCl3) δ 8.56 (d, J=1.4, 2H), 8.16 (dd, J=8.0, 1.4, 1H), 7.65-7.58 (m, 1H), 7.56-7.49 (m, 1H), 7.48-7.39 (m, 1H), 7.38-7.31 (m, 3H), 5.18 (s, 2H), 3.64-3.52 (m, 1H), 2.99-2.87 (m, 2H), 2.81-2.69 (m, 1H), 2.61-2.41 (m, 4H), 1.18 (d, J=6.8, 3H).

Workup

  1. customThe title compound was prepared
  2. concentrationThe reaction mixture was concentrated to dryness
  3. customthe residue subjected to HPLC purification

Sources & evidence

ORD record
ord-388c40476dc44020a8ca07bd58f0d021
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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