Water → HCID 59708428, compound

HRID 1641351Notes

Reaction equation

HRID 1641351 reaction equation
Cl[C:2]1[C:3]2[S:23](=[O:24])[CH2:22][CH2:21][C:4]=2[N:5]=[C:6]([N:8]2[CH2:13][CH2:12][N:11]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)[CH2:10][CH2:9]2)[N:7]=1.[N:25]1[C:33]2[CH:32]=[CH:31][N:30]=[CH:29][C:28]=2[NH:27][C:26]=1[CH2:34][NH2:35].C(N(C(C)C)CC)(C)C.O>O1CCOCC1>[Cl:20][C:17]1[CH:18]=[CH:19][C:14]([N:11]2[CH2:12][CH2:13][N:8]([C:6]3[N:7]=[C:2]([NH:35][CH2:34][C:26]4[NH:27][C:28]5[CH:29]=[N:30][CH:31]=[CH:32][C:33]=5[N:25]=4)[C:3]4[S:23](=[O:24])[CH2:22][CH2:21][C:4]=4[N:5]=3)[CH2:9][CH2:10]2)=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 337265671-(3H-Imidazo[4,5-c]pyridin-2-yl)methanamineHCID 594758954-Chloro-2-[4-(4-chloro-phenyl)-piperazin-1-yl]-6,7-dihydro-thieno[3,2-d]pyrimidine 5-oxide

Product 1

HCID 59708428HCID 59708428, compoundYield 19.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

200 mg 4-chloro-2-[4-(4-chloro-phenyl)-piperazin-1-yl]-6,7-dihydro-thieno[3,2-d]pyrimidine 5-oxide (cf Example 124), 346.22 mg C-(3H-imidazo[4,5-c]pyridin-2-yl)-methylamine and 359.24 μl diisopropylethylamine are placed in 4 ml dioxane, heated to 120° C. in the microwave for 0.3 hours and heated for another 0.3 hours at 120° C. Then the reaction mixture is mixed with water. The precipitated substance is suction filtered and washed with water. The product is purified by semipreparative HPLC (method A). 50 mg of the product are obtained as a powder. Analytical HPLC-MS (method B): RT=1.55 min.

Workup

  1. temperatureheated for another 0.3 hours at 120° C
  2. filtrationfiltered
  3. washwashed with water
  4. customThe product is purified by semipreparative HPLC (method A)

Sources & evidence

ORD record
ord-64992dfa984640b8b079c8ed43b74ea8
Source dataset
uspto-grants-2012_02
Patent number
US08114878B2

Reaction notes

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