Benzeneethanamine, 4-(iodo-125I)-2,5-dimethoxy- → (+/-) N-Methyl-N-(3-{[2-(10-trifluoroacetyl-10-aza-tricyclo[6.3.1.02.7]dodeca-2(7),3,5-trien-4-ylamino)-5-trifluoromethyl-pyrimidin-4-ylamino]-methyl}-pyridin-2-yl)-methanesulfonamide

HRID 1161646Notes

Reaction equation

HRID 1161646 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:10](=[CH:11][CH:12]=1)[CH:9]1[CH2:13][CH:5]2[CH2:6][N:7]([C:14](=[O:19])[C:15]([F:18])([F:17])[F:16])[CH2:8]1.Cl[C:21]1[N:26]=[C:25]([NH:27][CH2:28][C:29]2[C:30]([N:35]([CH3:40])[S:36]([CH3:39])(=[O:38])=[O:37])=[N:31][CH:32]=[CH:33][CH:34]=2)[C:24]([C:41]([F:44])([F:43])[F:42])=[CH:23][N:22]=1.COC1C(CCN)=CC(OC)=C([125I])C=1>O1CCOCC1>[CH3:40][N:35]([C:30]1[C:29]([CH2:28][NH:27][C:25]2[C:24]([C:41]([F:44])([F:42])[F:43])=[CH:23][N:22]=[C:21]([NH:1][C:2]3[CH:12]=[CH:11][C:10]4[CH:9]5[CH2:13][CH:5]([CH2:6][N:7]([C:14](=[O:19])[C:15]([F:18])([F:16])[F:17])[CH2:8]5)[C:4]=4[CH:3]=3)[N:26]=2)=[CH:34][CH:33]=[CH:32][N:31]=1)[S:36]([CH3:39])(=[O:37])=[O:38]

Participants

5

Reactant 3

HCID 195464Benzeneethanamine, 4-(iodo-125I)-2,5-dimethoxy-HCID 218647163-(trifluoroacetyl)-2,3,4,5-tetrahydro-1H-1,5-methano3-benzazepin-7-amineHCID 57584561N-(3-((2-chloro-5-(trifluoromethyl)pyrimidin-4-ylamino)methyl)pyridin-2-yl)-N-methylmethanesulfonamide

Product 1

HCID 86623360(+/-) N-Methyl-N-(3-{[2-(10-trifluoroacetyl-10-aza-tricyclo[6.3.1.02.7]dodeca-2(7),3,5-trien-4-ylamino)-5-trifluoromethyl-pyrimidin-4-ylamino]-methyl}-pyridin-2-yl)-methanesulfonamideYield 20%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 1-(4-Amino-10-aza-tricyclo[6.3.1.02.7]dodeca-2,4,6-trien-10-yl)-2,2,2-trifluoro-ethanone (158 g, 0.624 mmol) (see International Publication Nos. WO01/076576A2, WO01/062736A1, WO99/35131 and European Patent No. EP 1078637), 1,4-dioxane (1.00 mL), N-{3-[(2-Chloro-5-trifluoromethyl-pyrimidin-4-ylamino)-methyl]-pyridin-2-yl}-N-methyl-methanesulfonamide (247 mg, 0.624 mmol) and DIAE (255 mL, 1.47 mmol) was heated to 110° C. under a gentle flow of nitrogen. After sixteen hours, the mixture was concentrated, and the resulting residue was purified over silica (95:5:0.5 CHCl3:CH3OH:NH4OH) to provide (+/−) N-Methyl-N-(3-{[2-(10-trifluoroacetyl-10-aza-tricyclo[6.3.1.02.7]dodeca-2(7),3,5-trien-4-ylamino)-5-trifluoromethyl-pyrimidin-4-ylamino]-methyl}-pyridin-2-yl)-methanesulfonamide (3) as a white foam (78 mg, 0.124 mmol, 20%). C26H25F6N7O3S LC/MS (Method F) 630.3 (MH+); 19F NMR (D6-DMSO) δ −60.38, −67.99 (1:1 ratio) ppm.

Workup

  1. waitAfter sixteen hours
  2. concentrationthe mixture was concentrated
  3. customthe resulting residue was purified over silica (95:5:0.5 CHCl3:CH3OH:NH4OH)

Sources & evidence

ORD record
ord-93fe840f3d1348e7a64f6710a4952b83
Source dataset
uspto-grants-2010_10
Patent number
US07820648B2

Reaction notes

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