HCID 58864274, compound → HCID 178432157, compound

HRID 2355878Notes

Reaction equation

HRID 2355878 reaction equation
C[O:2][C:3](=[O:45])[C@H:4]([NH:25][C:26]([N:28]1[CH2:33][CH2:32][CH:31]([N:34]2[CH2:43][C:42]3[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=3)[NH:36][C:35]2=[O:44])[CH2:30][CH2:29]1)=[O:27])[CH2:5][C:6]1[CH:24]=[CH:23][C:9]2[N:10](S(CC[Si](C)(C)C)(=O)=O)[C:11]([CH3:13])=[N:12][C:8]=2[CH:7]=1.COC(=O)[C@H](NC(N1CCC(N2CC3C(=CC=CC=3)NC2=O)CC1)=O)CC1C=CC2N=C(C)N(S(CC[Si](C)(C)C)(=O)=O)C=2C=1.O=C1N(C2CCN(C(N[C@H](CC3C=C4C(=CC=3)N(S(CC[Si](C)(C)C)(=O)=O)N=C4)C(O)=O)=O)CC2)CC2C(=CC=CC=2)N1.[OH-].[Li+].CO.O1CCCC1.O>>[CH3:13][C:11]1[NH:10][C:9]2[CH:23]=[CH:24][C:6]([CH2:5][C@@H:4]([NH:25][C:26]([N:28]3[CH2:29][CH2:30][CH:31]([N:34]4[CH2:43][C:42]5[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=5)[NH:36][C:35]4=[O:44])[CH2:32][CH2:33]3)=[O:27])[C:3]([OH:45])=[O:2])=[CH:7][C:8]=2[N:12]=1

Participants

5

Reactant 4

HCID 58864274HCID 58864274, compoundHCID 58864319(R)-3-[2-Methyl-1-(2-trimethylsilanyl-ethanesulfonyl)-1H-benzoimidazol-5-yl]-2-{[4-(2-oxo-1,4-dihydro-2H-quinazolin-3-yl)-piperidine-1-carbonyl]-amino}-propionic acid methyl esterHCID 58864337HCID 58864337, compoundHCID 68706663HCID 68706663, compound

Product 1

HCID 178432157HCID 178432157, compound

Procedure

The 1:1 mixture of (R)-3-[2-Methyl-1-(2-trimethylsilanyl-ethanesulfonyl)-1H-benzoimidazol-5-yl]-2-{[4-(2-oxo-1,4-dihydro-2H-quinazolin-3-yl)-piperidine-1-carbonyl]-amino}-propionic acid methyl ester and (R)-3-[2-Methyl-3-(2-trimethylsilanyl-ethanesulfonyl)-3H-benzoimidazol-5-yl]-2-{[4-(2-oxo-1,4-dihydro-2H-quinazolin-3-yl)-piperidine-1-carbonyl]-amino}-propionic acid methyl ester was treated as described above for (R)-2-{[4-(2-oxo-1,4-dihydro-2H-quinazolin-3-yl)-piperidine-1-carbonyl]-amino}-3-[1-(2-trimethylsilanyl-ethanesulfonyl)-1H-indazol-5-yl]-propionic acid. The hydrolysis conditions (lithium hydroxide/methanol-tetrahydrofuran-water (1:1:1) at −15° C. overnight were used. The title compound was obtained as a white solid (25%). Mass spec.: 477.24 (MH)+.

Workup

  1. additionwas treated

Sources & evidence

ORD record
ord-adf5a740ca414ce793594c00f57f48e1
Source dataset
uspto-grants-2010_07
Patent number
US07754732B2

Reaction notes

Loading…