Amantadine → HCID 178508599, compound

HRID 2053009Notes

Reaction equation

HRID 2053009 reaction equation
[NH2:1][C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH2:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH:12]=3)=[CH:9][N:8]([C@H:25]3[CH2:28][C@H:27]([CH2:29]OS(C4C=CC(C)=CC=4)(=O)=O)[CH2:26]3)[C:4]=2[N:5]=[CH:6][N:7]=1.[C:41]12([NH2:51])[CH2:50][CH:45]3[CH2:46][CH:47]([CH2:49][CH:43]([CH2:44]3)[CH2:42]1)[CH2:48]2>CN(C)C=O>[C:41]12([NH:51][CH2:29][C@H:27]3[CH2:26][C@H:25]([N:8]4[C:4]5[N:5]=[CH:6][N:7]=[C:2]([NH2:1])[C:3]=5[C:10]([C:11]5[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH2:18][C:19]6[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=6)[CH:12]=5)=[CH:9]4)[CH2:28]3)[CH2:48][CH:47]3[CH2:46][CH:45]([CH2:44][CH:43]([CH2:49]3)[CH2:42]1)[CH2:50]2

Participants

4

Reactant 2

HCID 2130Amantadine2×HCID 178427768HCID 178427768, compound

Product 1

HCID 178508599HCID 178508599, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

50 mg (0.09 mmol) of trans-toluene-4-sulfonic acid 3-[4-amino-5-(3-benzyloxy-phenyl)-pyrrolo[2,3-d]pyrimidin-7-yl]-cyclobutylmethyl ester and 34 mg (0.225 mmol) of adamantan-1-ylamine (Fluka, Buchs, Switzerland) in 1 ml N,N-dimethylformamide are stirred for 18 h at RT and for 24 h at 60° C. Additional adamantan-1-ylamine is added (34 mg) and stirring is continued for 24 h at 120° C. The solvent is evaporated to dryness and the residue is purified by flash-chromatography (ethylacetate:methanol:NH4OHaqu.=95:5:1) to provide trans-7-[3-(adamantan-1-ylaminomethyl)cyclobutyl]-5-(3-benzyloxy-phenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine. Analytical HPLC: tR=11.14 min (Grad 1); ES-MS: m/eo=533.9.

Workup

  1. customThe solvent is evaporated to dryness
  2. customthe residue is purified by flash-chromatography (ethylacetate:methanol:NH4OHaqu.=95:5:1)

Sources & evidence

ORD record
ord-40f5cecede694fdba5c3cadd5176a100
Source dataset
uspto-grants-2008_02
Patent number
US07326699B2

Reaction notes

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