Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → N-(4-Fluoro-2-(methylcarbamoyl)benzyl)-3-(benzyloxy)-8,8-dimethyl-4-oxo-4,6,7,8-tetrahydropyrrolo[1,2-a]pyrimidine-2-carboxamide

HRID 346480ノート

反応式

HRID 346480 の反応式
[CH2:1]([O:8][C:9]1[C:14](=[O:15])[N:13]2[CH2:16][CH2:17][C:18]([CH3:20])([CH3:19])[C:12]2=[N:11][C:10]=1[C:21](O)=[O:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.FC(F)(F)C(O)=O.[NH2:55][CH2:56][C:57]1[CH:66]=[CH:65][C:64]([F:67])=[CH:63][C:58]=1[C:59]([NH:61][CH3:62])=[O:60]>CN(C=O)C.CN(C)C1C=CN=CC=1>[F:67][C:64]1[CH:65]=[CH:66][C:57]([CH2:56][NH:55][C:21]([C:10]2[N:11]=[C:12]3[C:18]([CH3:19])([CH3:20])[CH2:17][CH2:16][N:13]3[C:14](=[O:15])[C:9]=2[O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:22])=[C:58]([C:59](=[O:60])[NH:61][CH3:62])[CH:63]=1

参加物

6

反応物 3

HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 210698142-(Aminomethyl)-5-fluoro-n-methylbenzamide trifluoroacetate saltHCID 210801683-(Benzyloxy)-8,8-dimethyl-4-oxo-4,6,7,8-tetrahydropyrrolo[1,2-a]pyrimidine-2-carboxylic acid

生成物 1

HCID 21080176N-(4-Fluoro-2-(methylcarbamoyl)benzyl)-3-(benzyloxy)-8,8-dimethyl-4-oxo-4,6,7,8-tetrahydropyrrolo[1,2-a]pyrimidine-2-carboxamide収率 95%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒2 回HCID 6228Dimethylformamide溶媒2 回

実験手順

Intermediate 6, 3-(benzyloxy)-8,8-dimethyl-4-oxo-4,6,7,8-tetrahydropyrrolo[1,2-a]pyrimidine-2-carboxylic acid, (79 mg, 0.25 mmol) was placed together with O-(7-azobenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate, HATU, (114 mg, 0.3 mmol) in 2 mL DMF under N2 and stirred for 20 min. 4-(Dimethylamino)pyridine, DMAP, (100 mg, 0.8 mmol) and intermediate 3, 2-aminomethyl-5-fluoro-N-methylbenzamide trifluoroacetic acid salt (89 mg, 0.3 mmol) in 1 mL DMF were added and stirring continued for 20 min. The reaction mixture was concentrated, the residue dissolved in CH2Cl2 and washed with H2O. The CH2Cl2 layer was separated, dried (MgSO4), filtered and concentrated to give 118 mg of a the title compound as a solid (Yield=95%). 1H NMR (300 MHz, CDCl3) δ ppm: 8.31–8.46 (1 H, m) 7.24–7.46 (5 H, m) 6.95–7.15 (3 H, m) 6.88 (1 H, s) 5.23 (2 H, s) 4.48 (2 H, d, J=6.6 Hz) 3.95–4.10 (2 H, m) 2.93 (3 H, t, J=5.1 Hz) 2.00–2.16 (2 H, m) 1.34 (6 H, s); LC/MS m/z 479 (M+H).

後処理

  1. stirringstirring
  2. waitcontinued for 20 min
  3. concentrationThe reaction mixture was concentrated
  4. dissolutionthe residue dissolved in CH2Cl2
  5. washwashed with H2O
  6. customThe CH2Cl2 layer was separated
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-d94e459a691c43008f302d8db8efddb0
出典データセット
uspto-grants-2007_02
特許番号
US07173022B2

反応ノート

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