Diisopropylethylamine → HCID 53247239, compound

HRID 1476540Notes

Reaction equation

HRID 1476540 reaction equation
F[C:2](F)(F)[C:3]([OH:5])=O.[CH3:8][O:9][CH2:10][N:11]1[C:15]([CH2:16][N:17]2[C:22]3[CH:23]=[C:24]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[S:25]C=3C(=O)[N:19]([CH:33]3[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]3)[C:18]2=[O:39])=[N:14][N:13]=[N:12]1.[CH2:40]([O:42][C:43]1[C:52]([O:53][CH3:54])=[CH:51][C:50]2[C:49]([C:55]3[CH:63]=[CH:62][C:58]([C:59]([OH:61])=O)=[CH:57][CH:56]=3)=[N:48][C@@H:47]3[CH2:64][CH2:65][S:66][CH2:67][C@@H:46]3[C:45]=2[CH:44]=1)[CH3:41].[B-](F)(F)(F)F.CCOC(C(C#N)=NOC(N(C)C)=[N+](C)C)=O.C1C=NC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>C(Cl)Cl>[CH2:40]([O:42][C:43]1[C:52]([O:53][CH3:54])=[CH:51][C:50]2[C:49]([C:55]3[CH:56]=[CH:57][C:58]([C:59]([N:36]4[CH2:35][CH2:34][CH:33]([N:19]5[C:3](=[O:5])[C:2]6[S:25][C:24]([C:26]7[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=7)=[CH:23][C:22]=6[N:17]([CH2:16][C:15]6[N:11]([CH2:10][O:9][CH3:8])[N:12]=[N:13][N:14]=6)[C:18]5=[O:39])[CH2:38][CH2:37]4)=[O:61])=[CH:62][CH:63]=3)=[N:48][C@@H:47]3[CH2:46][CH2:67][S:66][CH2:65][C@@H:64]3[C:45]=2[CH:44]=1)[CH3:41]

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 181649HOAt2×HCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborate2×HCID 672590924-[(4aR,10bR)-9-ethoxy-8-methoxy-3,4,4a,10b-tetrahydro-1H-thiopyrano[4,3-c]isoquinolin-6-yl]benzoic acid2×HCID 67262013HCID 67262013, compound

Product 1

HCID 53247239HCID 53247239, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound is prepared analogously as described for example 28 using 1-{[1-(methoxymethyl)-1H-tetrazol-5-yl]methyl}-6-phenyl-3-(piperidin-4-yl)thieno[3,2-d]pyrimidine-2,4(1H,3H)-dione trifluoroacetate (compound B48) (235 mg), 4-[(4aR,10bR)-9-ethoxy-8-methoxy-3,4,4a,10b-tetrahydro-1H-thiopyrano[4,3-c]isoquinolin-6-yl]benzoic acid (165 mg; compound C10), TOTU (177 mg), HOAT (85 mg) and DIPEA (214 mg) in DCM (8 ml). After stirring for 4.5 h at RT additional 4-[(4aR,10bR)-9-ethoxy-8-methoxy-3,4,4a,10b-tetrahydro-1H-thiopyrano[4,3-c]isoquinolin-6-yl]benzoic acid (82.5 mg; compound C10), TOTU (177 mg) and HOAT (85 mg) are added. Purification by flash column chromatography [amino phase silica gel, eluation gradient: cyclohexane/EtOAc, 100/0 to 0/100 (v/v)] gives the title compound as a solid.

Workup

  1. customThe title compound is prepared analogously
  2. additionare added
  3. customPurification by flash column chromatography [amino phase silica gel, eluation gradient: cyclohexane/EtOAc, 100/0 to 0/100 (v/v)]

Sources & evidence

ORD record
ord-d4ff55caf7154a7ab92375b31528e761
Source dataset
uspto-grants-2015_04
Patent number
US09018175B2

Reaction notes

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