Dimethyl Sulfoxide → HCID 69962563, compound

HRID 2300880Notes

Reaction equation

HRID 2300880 reaction equation
[C:1]1([C@@H:7]([NH:9][C:10]2[N:15]=[C:14]([N:16]3[C:20]4[CH:21]=[CH:22][C:23]([C:25]5[CH:30]=[CH:29][N:28]=[C:27](Cl)[N:26]=5)=[CH:24][C:19]=4[N:18]=[CH:17]3)[CH:13]=[CH:12][N:11]=2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[CH3:33][O:34][C:35]1[CH:36]=[C:37]([CH:40]=[C:41]([O:45][CH3:46])[C:42]=1[O:43][CH3:44])[CH2:38][NH2:39].C(N(CC)C(C)C)(C)C.CS(C)=O>O>[C:1]1([C@@H:7]([NH:9][C:10]2[N:15]=[C:14]([N:16]3[C:20]4[CH:21]=[CH:22][C:23]([C:25]5[CH:30]=[CH:29][N:28]=[C:27]([NH:39][CH2:38][C:37]6[CH:40]=[C:41]([O:45][CH3:46])[C:42]([O:43][CH3:44])=[C:35]([O:34][CH3:33])[CH:36]=6)[N:26]=5)=[CH:24][C:19]=4[N:18]=[CH:17]3)[CH:13]=[CH:12][N:11]=2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 16248209HCID 16248209, compoundHCID 59924709HCID 59924709, compound

Product 1

HCID 69962563HCID 69962563, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

2-[(S)-1-Phenylethylamino]-4-[5-(2-chloropyrimidin-4-yl)benzimidazol-1-yl]pyrimidine (EXAMPLE 424) (80 mg), 3,4,5-trimethoxybenzylamine hydrochloride (219 mg), and N,N-diisopropylethylamine (0.16 mL) were dissolved DMSO (4 mL) and the resulting solution was heated to 100° C. for 15 hours. Upon cooling the reaction mixture was diluted with water (20 mL) and extracted with EtOAc (2×25). The combined organic extracts were dried (MgSO4) and evaporated.

Workup

  1. temperatureUpon cooling the reaction mixture
  2. extractionextracted with EtOAc (2×25)
  3. dry with materialThe combined organic extracts were dried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-46e05d377b3b4fb7a265e8b319135b39
Source dataset
uspto-grants-2002_12
Patent number
US06498165B1

Reaction notes

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