Diisopropylethylamine → HCID 70976333, compound

HRID 1476560Notes

Reaction equation

HRID 1476560 reaction equation
Cl.[CH3:2][O:3][CH2:4][CH2:5][CH2:6][C:7]1[N:11]=[C:10]([CH2:12][N:13]2[C:18]3[CH:19]=[C:20]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[S:21][C:17]=3[C:16](=[O:28])[N:15]([CH:29]3[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]3)[C:14]2=[O:35])[O:9][N:8]=1.[CH2:36]([O:38][C:39]1[C:48]([O:49][CH3:50])=[CH:47][C:46]2[C:45]([C:51]3[CH:59]=[CH:58][C:54]([C:55](O)=[O:56])=[CH:53][CH:52]=3)=[N:44][C@@H:43]3[CH2:60][CH2:61][S:62][CH2:63][C@@H:42]3[C:41]=2[CH:40]=1)[CH3:37].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>C(Cl)Cl>[CH2:36]([O:38][C:39]1[C:48]([O:49][CH3:50])=[CH:47][C:46]2[C:45]([C:51]3[CH:52]=[CH:53][C:54]([C:55]([N:32]4[CH2:31][CH2:30][CH:29]([N:15]5[C:16](=[O:28])[C:17]6[S:21][C:20]([C:22]7[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=7)=[CH:19][C:18]=6[N:13]([CH2:12][C:10]6[O:9][N:8]=[C:7]([CH2:6][CH2:5][CH2:4][O:3][CH3:2])[N:11]=6)[C:14]5=[O:35])[CH2:34][CH2:33]4)=[O:56])=[CH:58][CH:59]=3)=[N:44][C@@H:43]3[CH2:60][CH2:61][S:62][CH2:63][C@@H:42]3[C:41]=2[CH:40]=1)[CH3:37]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 672582531-{[3-(3-methoxypropyl)-1,2,4-oxadiazol-5-yl]methyl}-6-phenyl-3-(piperidin-4-yl)thieno[3,2-d]pyrimidine-2,4(1H,3H)-dione hydrochlorideHCID 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 70976333HCID 70976333, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-{[3-(3-methoxypropyl)-1,2,4-oxadiazol-5-yl]methyl}-6-phenyl-3-(piperidin-4-yl)thieno[3,2-d]pyrimidine-2,4(1H,3H)-dione hydrochloride (210 mg; compound B90) is reacted with 4-[(4aR,10bR)-9-ethoxy-8-methoxy-3,4,4a,10b-tetrahydro-1H-thiopyrano[4,3-c]isoquinolin-6-yl]benzoic acid (159 mg; compound C10) and HBTU (167 mg) in DCM (3.5 ml) in the presence of DIPEA (207 mg) according to the procedure described in example 2 to afford the title compound after purification by flash column chromatography [amino phase silica gel, eluent: EtOAc] as a solid.

Sources & evidence

ORD record
ord-895e1278db644be292893c5f76b7037c
Source dataset
uspto-grants-2015_04
Patent number
US09018175B2

Reaction notes

Loading…