1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 53246867, compound

HRID 1476531Notes

Reaction equation

HRID 1476531 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([N:10]1[CH:14]=[CH:13][C:12]([CH2:15][N:16]2[C:21]3[CH:22]=[C:23]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[S:24][C:20]=3[C:19](=[O:31])[N:18]([CH:32]3[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]3)[C:17]2=[O:38])=[N:11]1)[CH3:9].[CH2:39]([O:41][C:42]1[C:51]([O:52][CH3:53])=[CH:50][C:49]2[C:48]([C:54]3[CH:62]=[CH:61][C:57]([C:58](O)=[O:59])=[CH:56][CH:55]=3)=[N:47][C@@H:46]3[CH2:63][CH2:64][S:65][CH2:66][C@@H:45]3[C:44]=2[CH:43]=1)[CH3:40].CCN=C=NCCCN(C)C.C1C=C2N=NN(O)C2=CC=1.O.S([O-])(O)(=O)=O.[K+]>C(Cl)Cl>[CH2:39]([O:41][C:42]1[C:51]([O:52][CH3:53])=[CH:50][C:49]2[C:48]([C:54]3[CH:55]=[CH:56][C:57]([C:58]([N:35]4[CH2:34][CH2:33][CH:32]([N:18]5[C:19](=[O:31])[C:20]6[S:24][C:23]([C:25]7[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=7)=[CH:22][C:21]=6[N:16]([CH2:15][C:12]6[CH:13]=[CH:14][N:10]([CH2:8][CH3:9])[N:11]=6)[C:17]5=[O:38])[CH2:37][CH2:36]4)=[O:59])=[CH:61][CH:62]=3)=[N:47][C@@H:46]3[CH2:63][CH2:64][S:65][CH2:66][C@@H:45]3[C:44]=2[CH:43]=1)[CH3:40]

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide2×HCID 516920Potassium bisulfateHCID 27960291-Hydroxybenzotriazole hydrate2×HCID 67258255HCID 67258255, compoundHCID 672590924-[(4aR,10bR)-9-ethoxy-8-methoxy-3,4,4a,10b-tetrahydro-1H-thiopyrano[4,3-c]isoquinolin-6-yl]benzoic acid

Product 1

HCID 53246867HCID 53246867, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 1-[(1-ethyl-1H-pyrazol-3-yl)methyl]-6-phenyl-3-(piperidin-4-yl)thieno[3,2-d]pyrimidine-2,4(1H,3H)-dione trifluoroacetate (250 mg; compound B43), 4-[(4aR,10bR)-9-ethoxy-8-methoxy-3,4,4a,10b-tetrahydro-1H-thiopyrano[4,3-c]isoquinolin-6-yl]benzoic acid (181 mg; compound C10), EDCI (87 mg) and HOBT hydrate (61 mg) in DCM (15 ml) DIPEA (0.24 ml) is added. After 14 h at RT additional EDCI (87 mg) and HOBT hydrate (61 mg) are added and the reaction mixture is stirred for additional 3 d at RT. Aqueous potassium hydrogen sulfate solution (10% w/w) is added and the mixture is filtered using a phase separator. The organic layer is concentrated under reduced pressure and the residue is purified by flash column chromatography [silica gel, eluation gradient: DCM/MeOH, 1/0 to 1/1 (v/v)] to afford the title compound as a solid.

Workup

  1. additionis added
  2. filtrationthe mixture is filtered
  3. concentrationThe organic layer is concentrated under reduced pressure
  4. customthe residue is purified by flash column chromatography [silica gel, eluation gradient: DCM/MeOH, 1/0 to 1/1 (v/v)]

Sources & evidence

ORD record
ord-b7a405888b1b4ea68f6fefe2e06b194f
Source dataset
uspto-grants-2015_04
Patent number
US09018175B2

Reaction notes

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