Water → HCID 59708428, compound

HRID 1911059Notes

Reaction equation

HRID 1911059 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-2b0f243f758349bd81a9590764ff6fd9
Source dataset
uspto-grants-2013_12
Patent number
US08604039B2

Reaction notes

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