HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Water → [(R)-1-(6-chloro-1H-benzimidazol-2-yl)-2-methoxy-ethyl]-{2-[4-(4-chloro-phenyl)-piperazin-1-yl]-5-oxo-6,7-dihydro-5H-5lambda4-thieno[3,2-d]pyrimidin-4-yl}-amine

HRID 70107
Notes
Print preview

Reaction equation

HRID 70107 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.[Cl:25][C:26]1[CH:27]=[CH:28][C:29]2[N:33]=[C:32]([C@@H:34]([NH2:38])[CH2:35][O:36][CH3:37])[NH:31][C:30]=2[CH:39]=1.C(N(C(C)C)CC)(C)C.O>O1CCOCC1.ClCCl>[Cl:25][C:26]1[CH:27]=[CH:28][C:29]2[N:33]=[C:32]([C@@H:34]([NH:38][C:2]3[C:3]4[S:23](=[O:24])[CH2:22][CH2:21][C:4]=4[N:5]=[C:6]([N:8]4[CH2:9][CH2:10][N:11]([C:14]5[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=5)[CH2:12][CH2:13]4)[N:7]=3)[CH2:35][O:36][CH3:37])[NH:31][C:30]=2[CH:39]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 594758954-Chloro-2-[4-(4-chloro-phenyl)-piperazin-1-yl]-6,7-dihydro-thieno[3,2-d]pyrimidine 5-oxideHCID 59708426(1R)-1-(5-chloro-1H-benzimidazol-2-yl)-2-methoxyethylamine

Product 1

HCID 59708429
[(R)-1-(6-chloro-1H-benzimidazol-2-yl)-2-methoxy-ethyl]-{2-[4-(4-chloro-phenyl)-piperazin-1-yl]-5-oxo-6,7-dihydro-5H-5lambda4-thieno[3,2-d]pyrimidin-4-yl}-amine
Yield 37.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 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), 235 mg (R)-1-(6-chloro-1H-benzimidazol-2-yl)-2-methoxy-ethylamine and 179.62 μl diisopropylethylamine are placed in 4 ml dioxane, and the mixture is heated to 120° C. in the microwave for 0.3 hours. Then the reaction mixture is combined with water and dichloromethane and extracted. The product is purified by semipreparative HPLC (method A). 113 mg of the product are obtained as a powder. Analytical HPLC-MS, (method B): RT=1.88 min.

Workup

  1. extractionextracted
  2. customThe product is purified by semipreparative HPLC (method A)

Sources & evidence

ORD record
ord-d01a71046514423f8d801eb4965992b8
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08822474B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes