Water → MORPHOLINE-4-CARBOXYLIC ACID ((S)-1-{2-[4-(4-CHLORO-PHENYL)-PIPERAZIN-1-YL]-5-OXO-6,7-DIHYDRO-5H-5lambda4-THIENO[3,2-D]PYRIMIDIN-4-YL}-PYRROLIDIN-2-YLMETHYL)-AMIDE

HRID 1911069Notes

Reaction equation

HRID 1911069 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:20][CH2:19][N:18]([C:21]3[N:22]=[C:23]([N:31]4[CH2:35][CH2:34][CH2:33][C@H:32]4[CH2:36][NH2:37])[C:24]4[S:29](=[O:30])[CH2:28][CH2:27][C:25]=4[N:26]=3)[CH2:17][CH2:16]2)=[CH:11][CH:10]=1.C(N(CC)CC)C.[N:45]1([C:51](Cl)=[O:52])[CH2:50][CH2:49][O:48][CH2:47][CH2:46]1.O>ClCCl>[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:16][CH2:17][N:18]([C:21]3[N:22]=[C:23]([N:31]4[CH2:35][CH2:34][CH2:33][C@H:32]4[CH2:36][NH:37][C:51]([N:45]4[CH2:50][CH2:49][O:48][CH2:47][CH2:46]4)=[O:52])[C:24]4[S:29](=[O:30])[CH2:28][CH2:27][C:25]=4[N:26]=3)[CH2:19][CH2:20]2)=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 848104-Morpholinecarbonyl chlorideHCID 66735925HCID 66735925, compound

Product 1

HCID 59708432MORPHOLINE-4-CARBOXYLIC ACID ((S)-1-{2-[4-(4-CHLORO-PHENYL)-PIPERAZIN-1-YL]-5-OXO-6,7-DIHYDRO-5H-5lambda4-THIENO[3,2-D]PYRIMIDIN-4-YL}-PYRROLIDIN-2-YLMETHYL)-AMIDE

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

100 mg C-((S)-1-{2-[4-(4-chloro-phenyl)-piperazin-1-yl]-5-oxo-6,7-dihydro-5H-5λ4-thieno[3,2-d]pyrimidin-4-yl }-pyrrolidin-2-yl)-methylamine trifluoroacetate, Diastereomer 2 (Example 226) (see scheme 3, 3.17.2) are placed in 2 ml dichloromethane. While cooling with the ice bath 38 μl triethylamine and 28 μl 4-morpholinecarbonyl chloride are added. The reaction mixture is stirred for 12 hours at ambient temperature and then mixed with water. The organic phase is dried and evaporated to dryness. 121 mg of the product are obtained as a solid. Analytical HPLC-MS (method D): RT=1.18 min.

Workup

  1. additionare added
  2. customThe organic phase is dried
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-dfbc86236bb344feaff37401ba41a7bb
Source dataset
uspto-grants-2013_12
Patent number
US08604039B2

Reaction notes

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