Triethylamine → HCID 178498196, compound

HRID 1056480Notes

Reaction equation

HRID 1056480 reaction equation
[OH:1][C:2]1[C:7]([CH:8]([CH3:10])[CH3:9])=[CH:6][C:5]([CH2:11][CH2:12][CH2:13][C:14]([OH:16])=O)=[CH:4][C:3]=1[CH:17]([CH3:19])[CH3:18].F[P-](F)(F)(F)(F)F.N1([PH+](N2CCCC2)N2CCCC2)CCCC1.[Cl-].[CH3:44][O:45][C:46]([C:48]1[CH:53]=[CH:52][C:51]([N:54]=[N:55][C:56]2[CH:61]=[CH:60][C:59]([CH2:62][NH3+:63])=[CH:58][CH:57]=2)=[CH:50][CH:49]=1)=[O:47].C(N(CC)CC)C>CN(C1C=CN=CC=1)C.C(Cl)Cl.C(Cl)(Cl)Cl.C(Cl)(Cl)Cl.CO>[OH:1][C:2]1[C:3]([CH:17]([CH3:19])[CH3:18])=[CH:4][C:5]([CH2:11][CH2:12][CH2:13][C:14]([NH:63][CH2:62][C:59]2[CH:58]=[CH:57][C:56](/[N:55]=[N:54]/[C:51]3[CH:52]=[CH:53][C:48]([C:46]([O:45][CH3:44])=[O:47])=[CH:49][CH:50]=3)=[CH:61][CH:60]=2)=[O:16])=[CH:6][C:7]=1[CH:8]([CH3:9])[CH3:10]

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 22226026Tripyrrolidinophosphonium hexafluorophosphateHCID 568512964-(4-Hydroxy-3,5-diisopropylphenyl)butanoic acidHCID 86695989(4-((4-(Methoxycarbonyl)phenyl)diazenyl)phenyl)methanaminium chloride

Product 1

HCID 178498196HCID 178498196, compoundYield 57.4%

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent2×HCID 21584188Chloroform methanolSolvent

Procedure

Acid 8 (164 mg, 1.00 mmol), benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate (BOP, 884 mg, 2.00 mmol) and DMAP (12 mg, 0.10 mmol) were dissolved in methylene chloride (10 mL) and stirred at room temperature for 10 min. A solution of compound 4 (366 mg, 1.2 mmol) and triethylamine (505 mg, 5.0 mmol) in methylene chloride (15 mL) was added, and the reaction mixture was stirred at room temperature for 48 h. Aqueous work-up and chromatography on silica gel using chloroform and chloroform-methanol (3%) step-gradient as an eluent afforded pure 9 (296 mg, 57%) as orange crystals. 1H NMR (360 MHz, CDCl3): δ 8.18 (d, J=8.6 Hz, 2H), 7.93 (d, J=8.7 Hz, 2H), 7.91 (d, J=8.6 Hz, 2H), 7.43 (d, J=8.3 Hz, 2H), 6.85 (s, 2H), 5.83 (t, J=9.1 Hz, 1H), 4.73 (s, 1H), 4.53 (d, J=5.9 Hz, 2H), 3.96 (s, 3H), 3.11 (septet, J=6.9 Hz, 2H), 2.60 (t, J=7.8 Hz, 2H), 2.29 (t, J=7.6 Hz, 2H), 1.99 (q, J=7.6 Hz, 2H), 1.24 (d, J=6.9 Hz, 12H). 13C NMR (90.55 MHz, CDCl3): δ 173.23, 166.90, 155.42, 152.23, 148.52, 142.66, 133.99, 133.57, 132.17, 130.98, 128.85, 128.38, 123.87, 123.73, 123.01, 121.65, 120.13, 52.73, 43.56, 36.51, 35.45, 28.02, 27.51, 23.15. HRMS (m/z): [M+H]+ calcd. for C31H37N3O4 516.2857. found 516.2863.

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 48 h

Sources & evidence

ORD record
ord-a3e69b28956443acb418518a6b453f08
Source dataset
uspto-grants-2016_07
Patent number
US09399145B2

Reaction notes

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