Tetrahydrofuran → ((S)-1-Cyclohexyl-2-{(S)-2-[2-(2,3-dihydro-indol-1-yl)-pyridin-4-yl]-pyrrolidin-1-yl}-2-oxo-ethyl)-carbamic acid tert-butyl ester

HRID 1667631Notes

Reaction equation

[NH:1]1[CH2:5][CH2:4][CH2:3][C@H:2]1[C:6]1[CH:7]=C(C2C3C(=CC=CC=3)NC=2)C=N[CH:11]=1.C(OC(N(C)[C@@H](C)[C:30]([NH:32][C@@H:33]([CH:37]1[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]1)[C:34]([OH:36])=O)=[O:31])=O)(C)(C)C.[OH2:45].[Cl-].COC1N=[C:53](OC)[N:52]=[C:51]([N+:57]2(C)[CH2:62][CH2:61]O[CH2:59][CH2:58]2)N=1.[CH2:64]1[CH2:68]O[CH2:66][CH2:65]1>CCOC(C)=O>[C:6]([O:45][C:30](=[O:31])[NH:32][C@@H:33]([CH:37]1[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42]1)[C:34]([N:1]1[CH2:5][CH2:4][CH2:3][C@H:2]1[C:6]1[CH:11]=[CH:53][N:52]=[C:51]([N:57]2[C:58]3[C:59](=[CH:68][CH:64]=[CH:65][CH:66]=3)[CH2:61][CH2:62]2)[CH:7]=1)=[O:36])([CH3:7])([CH3:11])[CH3:2]

Participants

Conditions

Temperature: 20 °C

Procedure

To a solution of 3-((S)-5-Pyrrolidin-2-yl-pyridin-3-yl)-1H-indole 6 (78 mg, 0.30 mmole) and (S)-[(S)-2-(tert-Butoxycarbonyl-methyl-amino)-propionylamino]-cyclohexyl-acetic acid (111.6 mg, 0.33 mmole) in 5 ml of THF at 0° C., was added 4-(4,6-Dimethoxy-[1,3,5]triazin-2-yl)-4-methyl-morpholinium chloride hydrate (98.6 mg, 0.36 mmole) in one portion. After stirring at 20° C. for 2 hours, the reaction mixture was diluted with 30 mL of EtOAc, washed with 3×10 mL of water and concentration to give [(S)-1-(S)-1-Cyclohexyl-2-{(S)-2-[5-(1H-indol-3-yl)-pyridin-3-yl]-pyrrolidin-1-yl}-2-oxo-ethylcarbamoyl)-ethyl]-methyl-carbamic acid tert-butyl ester 7 (143.5 mg, crude) as pale yellow solid without further purification for next step.

Workup

washwashed with 3×10 mL of water and concentration

Sources & evidence

ORD record: ord-c13a2ef416dd4677814d79eb90e228d0
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08044209B2

Reaction notes

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