Fmoc-L-Tic-OH → 2-[1-cyclohexyl-2-(2-phenylquinoxalin-6-yl)benzimidazole-5-carbonyl]-3,4-dihydro-1H-isoquinoline-3-carboxylic acid

HRID 1788429Notes

Reaction equation

HRID 1788429 reaction equation
[CH:1]1([CH2:7][CH:8]([NH:12][C:13]([C:15]2[CH:45]=[CH:44][C:18]3[N:19]([CH:38]4[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]4)[C:20]([C:22]4[CH:23]=[C:24]5[C:29](=[CH:30][CH:31]=4)[N:28]=[C:27]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[CH:26]=[N:25]5)=[N:21][C:17]=3[CH:16]=2)=[O:14])[C:9]([OH:11])=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.N1(C(OCC2C3C(=CC=CC=3)C3C2=CC=CC=3)=O)CC2C(=CC=CC=2)C[C@H:47]1C(O)=O>>[CH:38]1([N:19]2[C:18]3[CH:44]=[CH:45][C:15]([C:13]([N:12]4[CH:8]([C:9]([OH:11])=[O:10])[CH2:7][C:1]5[C:6](=[CH:5][CH:4]=[CH:3][CH:2]=5)[CH2:47]4)=[O:14])=[CH:16][C:17]=3[N:21]=[C:20]2[C:22]2[CH:23]=[C:24]3[C:29](=[CH:30][CH:31]=2)[N:28]=[C:27]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:26]=[N:25]3)[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43]1

Participants

3

Reactant 2

HCID 978341Fmoc-L-Tic-OHHCID 52761673-Cyclohexyl-2-[[1-cyclohexyl-2-(2-phenylquinoxalin-6-yl)benzimidazole-5-carbonyl]amino]propanoic acid

Product 1

HCID 52761992-[1-cyclohexyl-2-(2-phenylquinoxalin-6-yl)benzimidazole-5-carbonyl]-3,4-dihydro-1H-isoquinoline-3-carboxylic acidYield 41%

Procedure

The general procedure described for Compound 242 was used with Fmoc-Tic Wang resin (143 mg, 0.7 mmol/g), producing 25 mg of the title compound (41% yield). MS: 606.22 (M−H+) HPLC Procedure A, retention time=17.18 min.

Sources & evidence

ORD record
ord-6f0029f5f5a74f9fb2c53ce9bc2035db
Source dataset
uspto-grants-2009_03
Patent number
US07511145B2

Reaction notes

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