Diisopropylethylamine → (S)-2-(2-(5-allyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetamido)-3-(3-bromophenyl)-N-(4-chlorophenyl)-N-methylpropanamide

HRID 1471659ノート

反応式

HRID 1471659 の反応式
[CH2:1]([C:4]1[N:8]([CH2:9][C:10]([O:12]C)=O)[N:7]=[C:6]([C:14]([F:17])([F:16])[F:15])[CH:5]=1)[CH:2]=[CH2:3].[NH2:18][C@@H:19]([CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([Br:38])[CH:33]=1)[C:20]([N:22]([C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=1)[CH3:23])=[O:21].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[CH2:1]([C:4]1[N:8]([CH2:9][C:10]([NH:18][C@@H:19]([CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([Br:38])[CH:33]=2)[C:20]([N:22]([C:24]2[CH:25]=[CH:26][C:27]([Cl:30])=[CH:28][CH:29]=2)[CH3:23])=[O:21])=[O:12])[N:7]=[C:6]([C:14]([F:17])([F:16])[F:15])[CH:5]=1)[CH:2]=[CH2:3]

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 90280507(S)-2-amino-3-(3-bromophenyl)-N-(4-chlorophenyl)-N-methylpropanamideHCID 90281162methyl 2-(5-allyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetate

生成物 1

HCID 90281299(S)-2-(2-(5-allyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetamido)-3-(3-bromophenyl)-N-(4-chlorophenyl)-N-methylpropanamide収率 24.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of methyl 2-(5-allyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetate (110 mg, 0.48 mmol) and (S)-2-amino-3-(3-bromophenyl)-N-(4-chlorophenyl)-N-methylpropanamide (194 mg, 0.48 mmol) in DMF (2 mL) was added HATU (228 mg, 0.6 mmol) and DIEA (193 mg, 1.5 mmol). Upon completion of the reaction, the product was purified by reverse phase HPLC eluting with acetonitrile/water (with 0.1% TFA) to afford (S)-2-(2-(5-allyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetamido)-3-(3-bromophenyl)-N-(4-chlorophenyl)-N-methylpropanamide (68 mg, 24%) as a solid. MS (m/z): 582.9 [M+H]+; HPLC retention time 4.52 min (2-98% acetonitrile:water with 0.05% trifluoroacetic acid).

後処理

  1. customUpon completion of the reaction
  2. customthe product was purified by reverse phase HPLC
  3. washeluting with acetonitrile/water (with 0.1% TFA)

出典と根拠

ORDレコード
ord-bd3bdf3a997d421aa75474e1d8a6268c
出典データセット
uspto-grants-2015_04
特許番号
US09012441B2

反応ノート

読み込み中…